Sodium Hydroxide → HCID 178461653, compound

HRID 732708Notes

Reaction equation

HRID 732708 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][N:24]([C:33]([NH:35][C@H:36]2[CH2:41][CH2:40][C@H:39]([C:42]([O:44]C)=[O:43])[CH2:38][CH2:37]2)=[O:34])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][N:24]([C:33]([NH:35][C@H:36]2[CH2:37][CH2:38][C@H:39]([C:42]([OH:44])=[O:43])[CH2:40][CH2:41]2)=[O:34])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501235HCID 178501235, compound

Product 1

HCID 178461653HCID 178461653, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 8.0 ml methanol solution of 330 mg of methyl trans-4-({[(3R,4S)-3-({(tert-butoxycarbonyl) [(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)cyclohexane-carboxylate was mixed with 1.5 ml of 1 M sodium hydroxide aqueous solution at room temperature and stirred overnight at room temperature. The solvent was evaporated under a reduced pressure, and the residue was mixed with 1 M hydrochloric acid, extracted with chloroform and dried with anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 176 mg of trans-4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)cyclohexane carboxylic acid as a colorless amorphous substance.

Workup

  1. customThe solvent was evaporated under a reduced pressure
  2. additionthe residue was mixed with 1 M hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-7dd4285e3f1d4f8c8f7874e82cd83890
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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