Potassium Carbonate → HCID 66975246, compound

HRID 1022637Notes

Reaction equation

[OH:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[O:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27][C@H:26]2[CH2:39]OS(C)(=O)=O)=[CH:21][C:20]=1[F:45]>COCCOC>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[O:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:27][C@H:26]2[CH2:39][N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]2=[O:1])=[CH:21][C:20]=1[F:45]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-hydroxypyridine-3-carboxylate (1.48 g) and potassium carbonate (2.23 g) were added to a solution of tert-butyl (6S,7R)-7-(4-chloro-3-fluorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (3.53 g) in 1,2-dimethoxyethane (70 ml). The reaction mixture was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.88 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, water
additionwas added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cdea681f59954f00b8ada60d92b0abe1
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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