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

Base Information

• Chemical Name: (S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate
• CAS No.: 866270-24-8
• Molecular Formula: C₂₇H₃₁BrN₂O₅
• Molecular Weight: 543.458
• Mol file: 866270-24-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate 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: 85.0%

(S)-N1-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N2-tert-butoxycarbonylvalinamide (866270-23-7) → (S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate (866270-24-8)

Guidance literature:

With iodine; triethylamine; triphenylphosphine; In dichloromethane; for 16h;

DOI:10.1021/jo0509760

Reference yield:

3-Bromophenylacetic acid (1878-67-7) → (S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate (866270-24-8)

Guidance literature:

Multi-step reaction with 8 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

8: 85 percent / triphenylphosphine; iodine; Et₃N / CH₂Cl₂ / 16 h

With dmap; lithium aluminium tetrahydride; thionyl chloride; rhodium (II) octanoate dimer; 4-acetamidobenzenesulfonyl azide; iodine; triethylamine; triphenylphosphine; tin(ll) chloride; In diethyl ether; dichloromethane; toluene; acetonitrile; 8: Robinson-Gabriel cyclodehydration reaction;

DOI:10.1021/jo0509760

Reference yield:

2-(3-bromophenyl)-N-methoxy-N-methylacetamide (866270-03-3) → (S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate (866270-24-8)

Guidance literature:

Multi-step reaction with 6 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

6: 85 percent / triphenylphosphine; iodine; Et₃N / CH₂Cl₂ / 16 h

With dmap; lithium aluminium tetrahydride; rhodium (II) octanoate dimer; 4-acetamidobenzenesulfonyl azide; iodine; triethylamine; triphenylphosphine; tin(ll) chloride; In diethyl ether; dichloromethane; toluene; acetonitrile; 6: Robinson-Gabriel cyclodehydration reaction;

DOI:10.1021/jo0509760

upstream raw materials:

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

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

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

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

Downstream raw materials:

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