Water → HCID 178472610, compound

HRID 1532352Notes

Reaction equation

HRID 1532352 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21]([C@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:22])[N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:35][OH:36].C(=O)([O-])[O-].[Na+].[Na+].O>CO>[OH:36][N:35]=[N:2][CH2:1][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21]([C@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:22])[N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 70106598HCID 70106598, compound

Product 1

HCID 178472610HCID 178472610, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

480 mg of ethyl 2-[(R)-2-[[(S)-2-[2-(6-cyano-1-ethylindol-2-yl)ethyl]pyrrolidinyl]carbonyl]pyrrolidinyl]acetate obtained in Example 60-a) was dissolved in methanol. 304 mg of hydroxylamine hydrochloride and 695 mg of sodium carbonate were added and the reaction solution was refluxed overnight with stirring. After water was added, the reaction solution was extracted two times with dichloromethane. The extract was dried over MgSO4 and distilled under reduced pressure. The residue was purified with silica gel column chromatography [eluent: dichloromethane/methanol(20:1)] to obtain 27 mg of the title compound.

Workup

  1. temperaturethe reaction solution was refluxed overnight
  2. extractionthe reaction solution was extracted two times with dichloromethane
  3. dry with materialThe extract was dried over MgSO4
  4. distillationdistilled under reduced pressure
  5. customThe residue was purified with silica gel column chromatography [eluent: dichloromethane/methanol(20:1)]

Sources & evidence

ORD record
ord-3b46a67574e74cc3ab9bec16b063cf9f
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

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