Hydrochloric Acid → HCID 57296591, compound

HRID 1166144Notes

Reaction equation

C([O:3][C:4](=[O:36])[CH2:5][C@H:6]1[O:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=2[O:21][CH3:22])[C:10]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:9]=2[N:8]([CH2:28][C:29]([CH2:33][OH:34])([CH3:32])[CH2:30][OH:31])[C:7]1=[O:35])C.[OH-].[Na+].O.Cl>C(O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:9]2[N:8]([CH2:28][C:29]([CH2:33][OH:34])([CH3:32])[CH2:30][OH:31])[C:7](=[O:35])[C@@H:6]([CH2:5][C:4]([OH:36])=[O:3])[O:12][C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=3[O:21][CH3:22])[C:10]=2[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (3R,5S)-7-chloro-1-(3-hydroxy-2-hydroxymethyl-2-methylpropyl)-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid ethyl ester (1.0 g) in ethanol (10 ml) was added a 1N aqueous solution of sodium hydroxide. The mixture was stirred at 60° C. for one hour. To the reaction mixture was added water, which was neutralized with 1N HCl, followed by subjecting to extraction with ethyl acetate. The extract solution was dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from a mixture of ethyl acetate and hexane to afford 0.38 g of (3R,5S)-7-chloro-1-(3-hydroxy-2-hydroxymethyl-2-methylpropyl)-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid, m.p. 208-210° C.

Workup

extractionby subjecting to extraction with ethyl acetate
dry with materialThe extract solution was dried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customthe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-cc7ffb28543e41a2b836352958e1ed9a
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613761B1

Reaction notes

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