(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
Hs Code.:

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

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

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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%

: 866270-23-7
(S)-N¹-[1-benzyloxycarbonyl-3-(3-bromophenyl)-2-oxopropyl]-N²-tert-butoxycarbonylvalinamide

: 866270-24-8
(S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate

Guidance literature:: With iodine; triethylamine; triphenylphosphine; In dichloromethane; for 16h;
DOI:10.1021/jo0509760

Reference yield:

: 1878-67-7
3-Bromophenylacetic acid

: 866270-24-8
(S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate

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:

: 866270-03-3
2-(3-bromophenyl)-N-methoxy-N-methylacetamide

: 866270-24-8
(S)-benzyl 5-(3-bromobenzyl)-[1-(tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxylate

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