methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

Base Information

Chemical Name:methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate
CAS No.:216302-14-6
Molecular Formula:C₁₉H₂₄N₂O₅S
Molecular Weight:392.476
Hs Code.:

Synonyms:methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

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Chemical Property of methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

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Technology Process of methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

There total 9 articles about methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-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: 98.0%

: 216302-15-7
methyl (2RS,4R)-2-[(1R,4R)-4-benzyloxycarbonylamino-4-carboxy-1-methylbutyl]thiazolidine-4-carboxylate

: 216302-14-6
methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

Guidance literature:: With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 5 ℃; for 5h;
DOI:10.1248/cpb.47.1532

Reference yield:

: 216302-09-9
methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate

: 216302-14-6
methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

: methyl (3R,6S,9R,9aS)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

Guidance literature:: methyl (2RS,4R)-2-[(1R,4S)-4-diphenylmethoxycarbonyl-4-benzyloxycarbonylamino-1-methylbutyl]thiazolidine-4-carboxylate; With methoxybenzene; trifluoroacetic acid; In tetrahydrofuran; at 30 ℃; for 3h;

With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; at 20 ℃; for 24h;
DOI:10.1248/cpb.47.1532

Reference yield:

: diphenylmethyl (2S)-N-benzyloxycarbonyl-5-methyl-6-oxopipecolate

: 216302-14-6
methyl (3R,6S,9R,9aR)-6-benzyloxycarbonylamino-9-methyl-5-oxooctahydroazepine[2,1-b]thiazole-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: LiAlH(t-BuO)3 / tetrahydrofuran; ethyl acetate / 2 h / 0 °C

2: AcONa; AcOH / ethanol; methanol; H₂O / 18 h / 20 °C

3: 32 percent / TFA; anisole / 1 h / 20 °C

4: 98 percent / Et₃N; ClCO₂Et / tetrahydrofuran / 5 h / 5 °C

With sodium acetate; chloroformic acid ethyl ester; acetic acid; methoxybenzene; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; 1: Reduction / 2: Condensation / 3: Deprotection / 4: Cyclization;
DOI:10.1248/cpb.47.1532