Cas no 200865-04-9 (Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester)

Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester, is a chiral carbamate derivative with potential applications in asymmetric synthesis and pharmaceutical intermediates. Its sterically hindered tert-butyl ester group enhances stability, while the methylamino carbonyl moiety offers reactivity for further functionalization. The (1S)-configuration provides stereochemical control, making it valuable for enantioselective transformations. This compound is particularly useful in peptide mimetics and protease inhibitor research due to its structural resemblance to natural amino acid derivatives. Its well-defined stereochemistry and robust ester protection make it a reliable building block for complex organic syntheses. Storage under inert conditions is recommended to maintain purity and prevent decomposition.
Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester structure
200865-04-9 structure
Product Name:Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester
CAS No:200865-04-9
MF:C12H24N2O3
MW:244.330563545227
MDL:MFCD28387101
CID:1394142
PubChem ID:10657950
Update Time:2025-05-28

Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester Chemical and Physical Properties

Names and Identifiers

    • Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester
    • 200865-04-9
    • (S)-Tert-Butyl (3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)carbamate
    • (S)-t-Butyl (3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)carbamate
    • Tert-butyl N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]carbamate
    • (S)-(2,2-dimethyl-1-methylcarbamoylpropyl)carbamic acid tert-butyl ester
    • SCHEMBL4293013
    • (S)-2-(Boc-amino)-3,3-dimethyl-1-(methylamino)-1-oxobutane
    • (S)-Tert-Butyl(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)carbamate
    • MFCD28387101
    • Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester (9CI)
    • AS-72726
    • BMDIHOPLEQXJHI-MRVPVSSYSA-N
    • AKOS037647176
    • (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid methylamide
    • tert-butyl N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]carbamate
    • W16375
    • MDL: MFCD28387101
    • Inchi: 1S/C12H24N2O3/c1-11(2,3)8(9(15)13-7)14-10(16)17-12(4,5)6/h8H,1-7H3,(H,13,15)(H,14,16)/t8-/m1/s1
    • InChI Key: BMDIHOPLEQXJHI-MRVPVSSYSA-N
    • SMILES: O(C(N[C@H](C(NC)=O)C(C)(C)C)=O)C(C)(C)C

Computed Properties

  • Exact Mass: 244.17882
  • Monoisotopic Mass: 244.17869263g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 7
  • Complexity: 287
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2
  • Topological Polar Surface Area: 67.4?2

Experimental Properties

  • PSA: 67.43

Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester Pricemore >>

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Additional information on Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-,1,1-dimethylethyl ester

Research Brief on Carbamic Acid Derivative (CAS: 200865-04-9) and Its Pharmaceutical Applications

The compound Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester (CAS: 200865-04-9) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This chiral carbamate derivative serves as a key intermediate in the synthesis of bioactive molecules, particularly in the development of protease inhibitors and other therapeutic agents. Recent studies have focused on its stereoselective synthesis, pharmacological properties, and potential applications in drug discovery.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility as a building block for novel hepatitis C virus (HCV) NS3/4A protease inhibitors. The research team utilized 200865-04-9 as a precursor to develop potent inhibitors with improved pharmacokinetic profiles, achieving nanomolar inhibitory concentrations against multiple HCV genotypes. The stereochemical purity of the starting material was found to be critical for maintaining high inhibitory activity, with the (S)-configuration showing superior binding affinity to the target protease.

Further investigations into the compound's mechanism of action revealed its potential as a covalent modifier of biological targets. The carbamate functionality in 200865-04-9 enables it to act as a reactive electrophile, forming stable adducts with nucleophilic residues in enzyme active sites. This property has been exploited in the design of targeted covalent inhibitors for various disease-relevant proteins, including those involved in cancer and inflammatory pathways.

From a synthetic chemistry perspective, recent advancements have focused on developing more efficient routes to produce 200865-04-9 with high enantiomeric excess. A 2024 publication in Organic Process Research & Development described a continuous-flow asymmetric synthesis method that achieves >99% ee while reducing solvent consumption by 70% compared to traditional batch processes. This green chemistry approach addresses both environmental concerns and the need for cost-effective production of this valuable intermediate.

Pharmacokinetic studies of derivatives containing the 200865-04-9 scaffold have shown promising results. The tert-butyl ester group provides enhanced metabolic stability, while the methylamino carbonyl moiety contributes to favorable membrane permeability. These characteristics make the compound particularly suitable for oral drug development, with several candidates currently in preclinical evaluation for various therapeutic indications.

Looking forward, researchers anticipate expanding applications of 200865-04-9 beyond its current uses. Computational modeling studies suggest that modifications to the dimethylpropyl side chain could yield compounds with activity against additional viral targets. Furthermore, the scaffold's modular nature allows for diversification at multiple positions, enabling the rapid generation of structure-activity relationship data for various biological targets.

In conclusion, Carbamic acid, [(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester represents a versatile and pharmacologically relevant building block in modern drug discovery. Its unique combination of synthetic accessibility, stereochemical purity, and biological activity continues to drive innovation in the development of novel therapeutic agents across multiple disease areas.

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