Cesium carbonate → ((6R,7S)-7-tert-butoxycarbonylamino-2-fluoro-6-methyl-8-oxo-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid methyl ester

HRID 1348612Notes

Reaction equation

HRID 1348612 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:11]=2[O:10][C@@H:9]1[CH3:21])([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:28][O:27][C:25](=[O:26])[CH2:24][N:13]1[C:12]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:11]=2[O:10][C@H:9]([CH3:21])[C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:22])[C:14]1=[O:15]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 67076781(6R,7S)-7-(Boc-amino)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten

Product 1

HCID 67076871((6R,7S)-7-tert-butoxycarbonylamino-2-fluoro-6-methyl-8-oxo-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid methyl esterYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.30 g (0.97 mmol) ((6R,7S)-2-Fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester in 8 ml dimethylformamide were stirred with 0.14 ml (1.45 mmol) methyl bromoacetate and 0.48 g (1.45 mmol) cesium carbonate overnight. Extraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:4 yielded 0.37 g (quant.) ((6R,7S)-7-tert-butoxycarbonylamino-2-fluoro-6-methyl-8-oxo-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-acetic acid methyl ester, MS m/e (%): 383.1 (M+H+, 14), 327.3 (24), 283.4 (199).

Workup

  1. extractionExtraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane 1:4

Sources & evidence

ORD record
ord-d071088a7e2c4a6689db57eca41cabf2
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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