4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[[(2,2,2-trichloroethoxy)carbonyl]thio]methyl]-, diphenylmethyl ester, (2S,5R,6S)-

Base Information

Chemical Name:4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[[(2,2,2-trichloroethoxy)carbonyl]thio]methyl]-, diphenylmethyl ester, (2S,5R,6S)-
CAS No.:615551-64-9
Molecular Formula:C25H24Cl3NO5S2
Molecular Weight:588.96
Hs Code.:

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,
3,3-dimethyl-7-oxo-6-[[[(2,2,2-trichloroethoxy)carbonyl]thio]methyl]-,
diphenylmethyl ester, (2S,5R,6S)-

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Chemical Property of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[[(2,2,2-trichloroethoxy)carbonyl]thio]methyl]-, diphenylmethyl ester, (2S,5R,6S)-

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Technology Process of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[[(2,2,2-trichloroethoxy)carbonyl]thio]methyl]-, diphenylmethyl ester, (2S,5R,6S)-

There total 5 articles about 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[[(2,2,2-trichloroethoxy)carbonyl]thio]methyl]-, diphenylmethyl ester, (2S,5R,6S)- 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: 83.0%

: 615551-62-7
(2S,5R,6S)-6-Mercaptomethyl-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 615551-64-9
(2S,5R,6S)-3,3-Dimethyl-7-oxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Guidance literature:: With dmap; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

: 908093-98-1
diazodiphenylmethane

: 615551-64-9
(2S,5R,6S)-3,3-Dimethyl-7-oxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / acetone / 14 h / 20 °C

2.1: t-BuMgBr / -78 °C

2.2: 36 percent / -78 - 20 °C

3.1: 89 percent / nBu₃SnH; AIBN / CH₂Cl₂

4.1: 74 percent / DMAP / CHCl₃ / 3 h

5.1: 77 percent / acetonitrile / 15 h / 20 °C

6.1: 85 percent / NaOMe / tetrahydrofuran; methanol / -78 - -40 °C

7.1: 83 percent / DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

With dmap; 2,2'-azobis(isobutyronitrile); tert-butylmagnesium bromide; tri-n-butyl-tin hydride; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetone; acetonitrile;
DOI:10.1016/j.bmcl.2003.12.037

Reference yield:

: 76517-80-1
diphenylmethyl 6β-(hydroxymethyl)penicillanate

: 615551-64-9
(2S,5R,6S)-3,3-Dimethyl-7-oxo-6-(2,2,2-trichloro-ethoxycarbonylsulfanylmethyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / DMAP / CHCl₃ / 3 h

2: 77 percent / acetonitrile / 15 h / 20 °C

3: 85 percent / NaOMe / tetrahydrofuran; methanol / -78 - -40 °C

4: 83 percent / DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

With dmap; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile;
DOI:10.1016/j.bmcl.2003.12.037