Water → HCID 57750143, compound

HRID 504571Notes

Reaction equation

HRID 504571 reaction equation
C([N:4]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([Cl:47])[CH:45]=2)[C@@:6]2([C@H:11]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[O:19][C:20]([CH2:30][CH3:31])([C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[O:24])[CH2:21][CH3:22])[CH2:10][C:9](=[O:32])[NH:8][C@@H:7]2[C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[CH3:40])[C:5]1=[O:48])(=O)C.[OH-].[Na+].O>CO>[Cl:47][C:44]1[CH:45]=[C:46]2[NH:4][C:5](=[O:48])[C@:6]3([C@H:11]([C:12]4[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=4[O:19][C:20]([CH2:30][CH3:31])([C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[O:24])[CH2:21][CH3:22])[CH2:10][C:9](=[O:32])[NH:8][C@@H:7]3[C:33]3[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:41]2=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 46852801HCID 46852801, compound

Product 1

HCID 57750143HCID 57750143, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At room temperature, a mixture of chiral (2′R,3R,4′S)-1-acetyl-6-chloro-4′-[5-chloro-2-(1-ethyl-1-methanesulfonylaminocarbonyl-propoxy)-phenyl]-2′-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (20 mg, 0.027 mmol) (RO5319796-000), NaOH (2 mg, 0.05 mmol), H2O (0.5 mL) and methanol (2 mL) was stirred overnight. Then methanol was removed by vacuum. The aqueous solution was acidified by addition of concentrated HCl to “pH” 1-2 and extracted with EtOAc twice. The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give the title compound as a white solid (10 mg).

Workup

  1. customThen methanol was removed by vacuum
  2. additionThe aqueous solution was acidified by addition of concentrated HCl to “
  3. extractionextracted with EtOAc twice
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0516b10b486346ffa9e06029e6d93a43
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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