Hydrochloric Acid → HCID 86632082, compound

HRID 504548Notes

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][C:24]([C:27]([O:29]C)=[O:28])([CH3:26])[CH3:25])[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[C:37]([CH3:38])=[CH:36][CH:35]=[C:34]([F:39])[C:33]=3[F:40])[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>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][C:24]([C:27]([OH:29])=[O:28])([CH3:25])[CH3:26])[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[C:37]([CH3:38])=[CH:36][CH:35]=[C:34]([F:39])[C:33]=3[F:40])[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of racemic (2′R,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(2,3-difluoro-6-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (110 mg, 0.18 mmol), NaOH (15 mg, 0.375 mmol), H2O (2 mL) and methanol (5 mL) was heated at 80° C. for 2 h. After cooled to room temperature, the solution was acidified to “pH” 1-2 by addition of concentrated aqueous HCl solution. The aqueous phase was extracted with EtOAc. The organic layer was separated, washed with water, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was washed with ether twice to give the title compound as a white solid (10 mg).

Workup

temperatureAfter cooled to room temperature
extractionThe aqueous phase was extracted with EtOAc
customThe organic layer was separated
washwashed with water
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customto give the crude product
washThe crude product was washed with ether twice

Sources & evidence

ORD record: ord-061c1d04c0104baa85dfb1f8c566468f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Reaction notes

Loading…