tert-butyl (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:tert-butyl (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.:768401-68-9
Molecular Formula:C₂₃H₃₂ClNO₅
Molecular Weight:437.964
Hs Code.:

Synonyms:tert-butyl (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 tert-butyl (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 tert-butyl (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 tert-butyl (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: 56.0%

: 190080-33-2
tert-butyl (2R)-2-(tert-butyl)-1,3-oxazol-3(2H)-carboxylate

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

: 768401-68-9
tert-butyl (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:: With triethylamine; In cyclohexane; at 60 ℃; for 4h;
DOI:10.1016/j.tet.2004.06.085

Reference yield:

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

: 768401-68-9
tert-butyl (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 5 steps

1: 86 percent / NaHCO₃ / methanol / 5 h / 50 °C

2: 94 percent / aq. KOH / methanol / 0 - 20 °C

3: 78 percent / benzene / 8 h / Heating

4: 68 percent / aq. KOH; NH₄Br / toluene / 6 h / Heating

5: 56 percent / Et₃N / cyclohexane / 4 h / 60 °C

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

Reference yield:

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

: 768401-68-9
tert-butyl (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: 56 percent / 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