2,6-Diazabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(3,4-dimethoxyphenyl)methyl]-7-oxo-, phenylmethyl ester, (1S,5R)-

Base Information

Chemical Name:2,6-Diazabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(3,4-dimethoxyphenyl)methyl]-7-oxo-, phenylmethyl ester, (1S,5R)-
CAS No.:145574-15-8
Molecular Formula:C22H24N2O5
Molecular Weight:396.443
Hs Code.:
Mol file:145574-15-8.mol

Synonyms:

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Chemical Property of 2,6-Diazabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(3,4-dimethoxyphenyl)methyl]-7-oxo-, phenylmethyl ester, (1S,5R)-

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Technology Process of 2,6-Diazabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(3,4-dimethoxyphenyl)methyl]-7-oxo-, phenylmethyl ester, (1S,5R)-

There total 5 articles about 2,6-Diazabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(3,4-dimethoxyphenyl)methyl]-7-oxo-, phenylmethyl ester, (1S,5R)- 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: 58.0%

: 214837-30-6
benzyl (1S,4S,5S)-6-(3,4-dimethoxybenzyl)-7-oxo-4-<(trifluoromethyl)sulfonyloxy>-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

: 145574-15-8
benzyl (1S,5R)-6-(3,4-dimethoxybenzyl)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/anie.200250348

Reference yield:

: 145574-13-6
benzyl (1S,4S,5S)-6-(3,4-dimethoxybenzyl)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

: 145574-15-8
benzyl (1S,5R)-6-(3,4-dimethoxybenzyl)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / pyridine / CH₂Cl₂

2: 58 percent / NaBH₄ / tetrahydrofuran; dimethylformamide

With pyridine; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200250348

Reference yield:

: [(2S,3S)-2-((R)-1,2-Dihydroxy-ethyl)-1-(3,4-dimethoxy-benzyl)-4-oxo-azetidin-3-yl]-carbamic acid benzyl ester

: 145574-15-8
benzyl (1S,5R)-6-(3,4-dimethoxybenzyl)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / tetrahydrofuran / 4 h / Heating

2: 86 percent / Bu₄NBr / dimethylformamide / 5 h / 140 °C

3: pyridine / CH₂Cl₂ / 2 h / below 10 deg C

4: NaBH₄ / tetrahydrofuran; dimethylformamide / 0 °C

With pyridine; sodium tetrahydroborate; tetrabutylammomium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm980023c