Sodium Hydroxide → 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoic acid

HRID 732711Notes

Reaction equation

HRID 732711 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:36]2[CH:45]=[CH:44][C:39]([C:40]([O:42]C)=[O:41])=[CH:38][C:37]=2[O:46][CH3:47])=[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+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:25][N:24]([C:33]([NH:35][C:36]2[CH:45]=[CH:44][C:39]([C:40]([OH:42])=[O:41])=[CH:38][C:37]=2[O:46][CH3:47])=[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])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68914214methyl 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoate

Product 1

HCID 689103484-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 243 mg of methyl 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoate and 6.0 ml of a THF-methanol (2:1) mixed solvent was mixed with 1.0 ml of 1 M sodium hydroxide aqueous solution at room temperature and stirred overnight at room temperature. The reaction solution was concentrated 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 227 mg of 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoic acid as a pale brown oily substance.

Workup

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

Sources & evidence

ORD record
ord-262aa16859404dc78d74ae2cd75fdcd0
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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