tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate
• CAS No.: 301544-38-7
• Molecular Formula: C₁₉H₃₀N₂O₄
• Molecular Weight: 350.458
• Mol file: 301544-38-7.mol

Synonyms:tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate

Chemical Property of tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate

There total 3 articles about tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-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: 78.0%

tert-butylisonitrile (119072-55-8,7188-38-7) + Boc-L-phenylalaninal (72155-45-4) → tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate (301544-38-7)

Guidance literature:

With 2,4,6-trimethyl-pyridine; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol0061485

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate (301544-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / HOBt; EDC; DIEA / acetonitrile

2: 99 percent / LiAlH₄ / tetrahydrofuran / -78 °C

3: 78 percent / 2,4,6-collidine; TFA / CH₂Cl₂ / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Acylation / 2: Reduction / 3: Passerini reaction;

DOI:10.1016/S0960-894X(00)00458-3

Reference yield:

Boc-Phe-OH N,O-dimethyl hydroxamate (87694-53-9) → tert-butyl ((2S)-4-(tert-butylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)carbamate (301544-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LiAlH₄ / tetrahydrofuran / -78 °C

2: 78 percent / 2,4,6-collidine; TFA / CH₂Cl₂ / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; lithium aluminium tetrahydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Passerini reaction;

DOI:10.1016/S0960-894X(00)00458-3

upstream raw materials:

tert-butylisonitrile

Boc-L-phenylalaninal

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Phe-OH N,O-dimethyl hydroxamate

Downstream raw materials:

C₃₆H₄₇N₉O₉S

(R)-5-Guanidino-2-phenylmethanesulfonylamino-pentanoic acid ({(S)-1-benzyl-2-hydroxy-2-[(phenethylcarbamoyl-methyl)-carbamoyl]-ethylcarbamoyl}-methyl)-methyl-amide

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid

2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid