(R)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Base Information

• Chemical Name: (R)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS No.: 115186-33-9
• Molecular Formula: C16H24N2O4
• Molecular Weight: 308.378
• Hs Code.: 2924299090
• ChEMBL ID: CHEMBL2374647
• DSSTox Substance ID: DTXSID20556352
• Mol file: 115186-33-9.mol

Synonyms:115186-33-9;(R)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate;N-Boc-D-phenylalanine N'-methoxy-N'-methylamide;N-[(1R)-2-(Methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl]carbamic Acid 1,1-Dimethylethyl Ester;tert-butyl N-[(2R)-1-[methoxy(methyl)amino]-1-oxo-3-phenylpropan-2-yl]carbamate;ZAHRDPIWMGLOQJ-CYBMUJFWSA-N;CHEMBL2374647;DTXSID20556352;(R)-tert-Butyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate;CS-0441377;F78755;Nalpha-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-D-phenylalaninamide;tert-butyl (1R)-1-benzyl-2-[methoxy(methyl)amino]-2-oxoethylcarbamate;Tert-butyl (R)-(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property of (R)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property:

• PSA: 71.36000
• LogP: 2.34660
• Storage Temp.: 2-8°C
• Solubility.: Methanol, DCM
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 308.17360725
• Heavy Atom Count: 22
• Complexity: 373

Purity/Quality:

98.5% ^*data from raw suppliers

N-[(1R)-2-(Methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl]carbamicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)N(C)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1)C(=O)N(C)OC
• Uses: N-[(1R)-2-(Methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl]carbamic Acid 1,1-Dimethylethyl Ester is an protected intermediate in the synthesis of Darunavir (D193500), a second generation HIV-1-protease inhibitor.

Technology Process of (R)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

There total 3 articles about (R)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Boc-D-Phe-OH (18942-49-9) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (R)-tert-butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (115186-33-9)

Guidance literature:

Boc-D-Phe-OH; With triethylamine; In dichloromethane; Inert atmosphere;

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Inert atmosphere;

N,O-dimethylhydroxylamine*hydrochloride; With triethylamine; Inert atmosphere;

DOI:10.1016/j.bmc.2011.04.047

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (R)-tert-butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (115186-33-9)

Guidance literature:

With 4-methyl-morpholine; In methanol; dichloromethane; water; isobutyl chloroformate;

Reference yield:

Boc-D-Phe-OH (18942-49-9) + N,0-dimethylhydroxylamine (1117-97-1) → (R)-tert-butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (115186-33-9)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide;

DOI:10.1016/S0960-894X(96)00559-8

upstream raw materials:

Boc-D-Phe-OH

N,O-dimethylhydroxylamine*hydrochloride

N,0-dimethylhydroxylamine

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(S)-(4-([1,1'-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)(2-benzylpiperidin-1-yl)methanone

(R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene

(R)-1-benzyl-prop-2-enylamine

(2S)-2-benzylpiperidine