methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

Base Information

Chemical Name:methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate
CAS No.:768401-67-8
Molecular Formula:C₂₀H₂₆ClNO₅
Molecular Weight:395.883
Hs Code.:

Synonyms:methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

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Chemical Property of methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

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Technology Process of methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

There total 7 articles about methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-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:

: 104173-34-4
2-t-butyl-3-methoxycarbonyl-2,3-dihydrooxazole

: 768401-42-9
4-benzyloxy-2-chlorobutanoyl chloride

: 768401-67-8
methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

: (1S,3R,5R,6S)-6-(2-Benzyloxy-ethyl)-3-tert-butyl-6-chloro-7-oxo-2-oxa-4-aza-bicyclo[3.2.0]heptane-4-carboxylic acid methyl ester

Guidance literature:: With triethylamine; In cyclohexane; at 60 ℃; for 4h; Title compound not separated from byproducts.;
DOI:10.1016/j.tet.2004.06.085

Reference yield:

: 31600-42-7
methyl 4-(benzyloxy)butanoate

: 768401-67-8
methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / n-BuLi; diisopropylamine; CCl₄ / tetrahydrofuran; hexane / 0.08 h / -78 °C

2: 93 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 0 °C

3: 90 percent / (COCl)2; DMF / CH₂Cl₂ / 0.5 h / 0 - 15 °C

4: Et₃N / cyclohexane / 4 h / 60 °C

With tetrachloromethane; lithium hydroxide; n-butyllithium; oxalyl dichloride; triethylamine; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water;
DOI:10.1016/j.tet.2004.06.085

Reference yield:

: 116842-10-5
(2R,4S)-(-)-Dimethyl-2-(1,1-dimethylethyl)-3,4-oxazolidindicarboxylat

: 768401-67-8
methyl (1S,3R,5R,7R)-3-(tert-butyl)-7-chloro-6-oxo-7-(2-benzyloxyethyl)-2-oxa-4-azabicyclo[3.2.0]heptane-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / aq. KOH / methanol / 0 - 20 °C

2: 84 percent / benzene / 8 h / Heating

3: 73 percent / aq. KOH; NH₄Br / toluene / 6 h / Heating

4: Et₃N / cyclohexane / 4 h / 60 °C

With potassium hydroxide; ammonium bromide; triethylamine; In methanol; cyclohexane; toluene; benzene;
DOI:10.1016/j.tet.2004.06.085