(S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide

Base Information

• Chemical Name: (S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide
• CAS No.: 866270-23-7
• Molecular Formula: C₂₇H₃₃BrN₂O₆
• Molecular Weight: 561.473
• Mol file: 866270-23-7.mol

Synonyms:(S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide

Chemical Property of (S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide

There total 8 articles about (S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide 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: 58.0%

benzyl 4-(3-bromophenyl)-2-diazo-3-oxo-butanoate (866270-22-6) + Boc-Val-NH2 (35150-08-4) → (S)-N1-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N2-tert-butoxycarbonylvalinamide (866270-23-7)

Guidance literature:

With rhodium (II) octanoate dimer; In dichloromethane; Heating;

DOI:10.1021/jo0509760

Reference yield:

3-Bromophenylacetic acid (1878-67-7) → (S)-N1-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N2-tert-butoxycarbonylvalinamide (866270-23-7)

Guidance literature:

Multi-step reaction with 7 steps

1: thionyl chloride / toluene / 1 h / Heating

2: 4.9 g / Et₃N / CH₂Cl₂ / 20 °C

3: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 71 percent / SnCl₂ / CH₂Cl₂ / 4 h

5: 67 percent / DMAP / toluene / 48 h / Heating

6: 78 percent / 4-acetamidobenzenesulfonyl azide; Et₃N / acetonitrile / 16 h / 20 °C

7: 58 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

With dmap; lithium aluminium tetrahydride; thionyl chloride; rhodium (II) octanoate dimer; 4-acetamidobenzenesulfonyl azide; triethylamine; tin(ll) chloride; In diethyl ether; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo0509760

Reference yield:

2-(3-bromophenyl)-N-methoxy-N-methylacetamide (866270-03-3) → (S)-N1-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N2-tert-butoxycarbonylvalinamide (866270-23-7)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

2: 71 percent / SnCl₂ / CH₂Cl₂ / 4 h

3: 67 percent / DMAP / toluene / 48 h / Heating

4: 78 percent / 4-acetamidobenzenesulfonyl azide; Et₃N / acetonitrile / 16 h / 20 °C

5: 58 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

With dmap; lithium aluminium tetrahydride; rhodium (II) octanoate dimer; 4-acetamidobenzenesulfonyl azide; triethylamine; tin(ll) chloride; In diethyl ether; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo0509760

upstream raw materials:

benzyl 4-(3-bromophenyl)-2-diazo-3-oxo-butanoate

Boc-Val-NH₂

2-(3-bromophenyl)-N-methoxy-N-methylacetamide

ethyl 4-(3-bromophenyl)-3-oxobutanoate

Downstream raw materials:

(S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate

(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate