Water → 6-chloro-4'-[5-chloro-2-(2-hydroxycarbonyl-2-methyl-propoxy)-phenyl]-2'-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504478Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][CH2:24][C:25]([C:28]([O:30]C)=[O:29])([CH3:27])[CH3:26])[CH2:14][C:13](=[O:32])[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][CH2:24][C:25]([C:28]([OH:30])=[O:29])([CH3:27])[CH3:26])[CH2:14][C:13](=[O:32])[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 330 mg racemic (2′R,3R,4′S)-6-chloro-4′-[5-chloro-2-(2-methoxycarbonyl-2-methyl-propoxy)-phenyl]-2′-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (330 mg, 0.55 mmol), NaOH (80 mg, 2 mmol), H2O (5 mL) and methanol (10 mL) was heated at 60° C. for 2 h. Then the methanol was removed in vacuum. The water solution was acidified by concentrated hydrochloric acid to “pH” 2. The white precipitate was collected by filtration to give title compound (Yield: 250 mg).

Workup

customThen the methanol was removed in vacuum
filtrationThe white precipitate was collected by filtration

Sources & evidence

ORD record: ord-631011d0e5744a2a8c93f5527e95bac2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Reaction notes

Loading…