Water → 6-{[(6RS,7SR)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]oxy}pyridine-2-carboxylic acid

HRID 1022723Notes

Reaction equation

[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH:12]2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([O:34]C)=[O:33])[N:27]=2)[CH:7]=[CH:8][C:9]=1[Cl:10].O>C(O)C>[C:21]([O:20][C:18]([N:14]1[CH2:13][CH:12]([O:25][C:26]2[N:27]=[C:28]([C:32]([OH:34])=[O:33])[CH:29]=[CH:30][CH:31]=2)[CH:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)[O:17][CH2:16][CH2:15]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

2M Aqueous sodium hydroxide solution (1.7 mL) was added to a solution of tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-{[6-(methoxycarbonyl)pyridin-2-yl]oxy}-1,4-oxazepane-4-carboxylate (210 mg) in ethanol (5 ml), and the mixture was stirred at room temperature overnight and at 70° C. for 2 hr. Water was added to the reaction mixture, and the mixture was washed with diethyl ether. The obtained aqueous layer was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (69 mg).

Workup

washthe mixture was washed with diethyl ether
extractionthe mixture was extracted with ethyl acetate
extractionThe obtained extract
washwas washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3a68a4cb0a7848aebf080baf94fa3f60
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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