tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Base Information

Chemical Name:tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
CAS No.:95991-81-4
Molecular Formula:C₁₈H₁₉ClN₂O₅
Molecular Weight:378.812
Hs Code.:

Synonyms:tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

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Chemical Property of tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

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Technology Process of tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

There total 8 articles about tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>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: 30.0%

: 95967-30-9
tert.-butyl (6R,7R)-7-benzoylamino-3-hydroxy-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

: 95991-81-4
tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:: With phosphorus trichloride; In N,N-dimethyl-formamide; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)88797-4

Reference yield:

: 87064-89-9
tert.-butyl 4-hydroxyacetoacetate

: 95991-81-4
tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 31 percent / boron trifluoride etherate / tetrahydrofuran / 0.5 h / Ambient temperature

2: 96 percent / triethylamine, p-toluenesulfonyl azide / acetonitrile / 1.5 h / Ambient temperature

3: 82 percent / rhodium(II) acetate / benzene / 1 h / 80 °C

4: 30 percent / phosphorus trichloride / dimethylformamide / 2 h / Ambient temperature

With 4-toluenesulfonyl azide; triethylamine; phosphorus trichloride; rhodium(II) acetate; boron trifluoride diethyl etherate; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)88797-4

Reference yield:

: 74530-56-6
tert-butyl 4-chloroacetoacetate

: 95991-81-4
tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 80percent sodium hydride / 1.) THF, paraffin oil, 0 deg C, 1 h, RT, 0.5 h; 2.) THF, 0 deg C, 1 h, RT, 1 h

2: 97 percent / H₂ / 10percent palladium/C / methanol / 1.5 h / Ambient temperature

3: 31 percent / boron trifluoride etherate / tetrahydrofuran / 0.5 h / Ambient temperature

4: 96 percent / triethylamine, p-toluenesulfonyl azide / acetonitrile / 1.5 h / Ambient temperature

5: 82 percent / rhodium(II) acetate / benzene / 1 h / 80 °C

6: 30 percent / phosphorus trichloride / dimethylformamide / 2 h / Ambient temperature

With 4-toluenesulfonyl azide; hydrogen; sodium hydride; triethylamine; phosphorus trichloride; rhodium(II) acetate; palladium on activated charcoal; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)88797-4