Dimethyl Sulfide → [(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

HRID 1348609Notes

Reaction equation

HRID 1348609 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][CH:17]=C)[C:12]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:11]=2[O:10][C@@H:9]1[CH3:24])([CH3:4])([CH3:3])[CH3:2].[O:26]=[O+][O-].CSC>ClCCl>[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][CH:17]=[O:26])[C:12]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:11]=2[O:10][C@@H:9]1[CH3:24])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67076945((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester

Product 1

HCID 86605287[(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.20 g (6.28 mmol) ((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester in 120 ml dichloromethane was treated with ozone at −75° C. for 20 minutes. Methyl sulfide, 2.27 g (30.6 mmol), was added and the solution was stirred for 4.5 hours at room temperature. The solvent was distilled off under vacuum and the residue was extracted with ethylacetate/water to yield 2.05 g crude [(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester, MS m/e (%): 353.2 (M+H+, 11), 297.3 (60), 253.2 (100).

Workup

  1. distillationThe solvent was distilled off under vacuum
  2. extractionthe residue was extracted with ethylacetate/water

Sources & evidence

ORD record
ord-1c1f7fbba99a4d3a9d15ae6a42bd7eaf
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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