p-nitrobenzyl (5R,7R)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-carboxylate
CAS No.:123468-22-4
Molecular Formula:C₁₉H₂₁N₃O₇S
Molecular Weight:435.458
Hs Code.:

Synonyms:p-nitrobenzyl (5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-carboxylate

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Chemical Property of p-nitrobenzyl (5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-carboxylate

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Technology Process of p-nitrobenzyl (5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-carboxylate

There total 8 articles about p-nitrobenzyl (5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-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: 84.0%

: 123457-14-7
p-nitrobenzyl (2S*,3R*,5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-3-benzoyloxy-1-azabicyclo<3.3.0>octane-2-carboxylate

: 123468-22-4
p-nitrobenzyl (5R*,7R*)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-4-thia-1-azabicyclo<3.3.0>oct-2-ene-2-carboxylate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4020(01)80055-7

Reference yield:

: 123457-14-7
(3R,6R,7aS)-2-Benzoyloxy-6-tert-butoxycarbonylamino-5-oxo-hexahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid 4-nitro-benzyl ester

: 123468-22-4
(6S,7aR)-6-tert-Butoxycarbonylamino-5-oxo-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1016/S0040-4020(01)80055-7

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 123468-22-4
(6S,7aR)-6-tert-Butoxycarbonylamino-5-oxo-5,6,7,7a-tetrahydro-pyrrolo[2,1-b]thiazole-3-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 108.6 g / NaOH / H₂O; diethyl ether / 2 h

2: dimethylformamide / 72 h / Ambient temperature

3: 68.8 g / NaOAc / acetic acid / 24 h / Ambient temperature

4: NaHCO₃ / dimethylformamide / 48 h / Ambient temperature

5: CCl₄

6: DBU / CH₂Cl₂

With sodium hydroxide; sodium acetate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrachloromethane; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80055-7