Water → HCID 77502920, compound

HRID 504483Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][CH:35]([C:37]([O:39]CC)=[O:38])[CH3:36])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.[OH-].[Na+].O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][CH:35]([C:37]([OH:39])=[O:38])[CH3:36])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of racemic (2′S,3S,4′R)-4′-[5-bromo-2-(2-ethoxycarbonyl-2-methyl-ethoxy)-phenyl]-6-chloro-2′-(5-chloro-2-methyl phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (200 mg, 0.3 mmol), NaOH (40 mg, 1 mmol), H2O (5 mL) and THF (5 mL) was heated at 80° C. for 2 h. Then THF was removed in vacuum. The water solution was acidified by concentrated hydrochloric acid (1.5 mL) to “pH” 2. The white precipitate was collected by filtration to give the title compound as a white solid (Yield: 100 mg).

Workup

customThen THF was removed in vacuum
filtrationThe white precipitate was collected by filtration

Sources & evidence

ORD record: ord-51cb9fa18dbc4a7989158f9426adc792
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Reaction notes

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