Carbon Dioxide → (S)-3-tert-Butoxycarbonylamino-4-oxo-5-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carboxylic acid cyclopropylmethyl ester

HRID 1372973Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][C:17]([F:20])([F:19])[F:18])[C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:26](=[O:28])=[O:27].Br[CH2:30][CH:31]1[CH2:33][CH2:32]1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH:31]1([CH2:30][O:27][C:26]([N:10]2[CH2:9][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:25])[C:14](=[O:15])[N:13]([CH2:16][C:17]([F:20])([F:19])[F:18])[C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:28])[CH2:33][CH2:32]1

Participants

Reactant 4

HCID 280Carbon Dioxide

HCID 10796Cesium carbonate

HCID 81503Bromomethylcyclopropane

HCID 69039568[(S)-2-Oxo-1-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 69039698(S)-3-tert-Butoxycarbonylamino-4-oxo-5-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-carboxylic acid cyclopropylmethyl ester

Procedure

In an analogous manner to that described in Example 106a, the reaction of [(S)-2-oxo-1-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester [Example 107b] with carbon dioxide and bromomethyl-cyclopropane in presence of cesium carbonate yielded the title compound as a white foam; MS: m/e=475 (M+NH4)+.

Sources & evidence

ORD record: ord-dd8b8e54edf64e04ba8c245aa3c0fd8d
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160875B2

Reaction notes

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