Sodium Hydroxide → HCID 68912635, compound

HRID 732629Notes

Reaction equation

HRID 732629 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](=[O:42])[CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40]C)=[O:39])[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:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:25][N:24]([C:33](=[O:42])[CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])[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 68913838HCID 68913838, compound

Product 1

HCID 68912635HCID 68912635, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 270 mg portion of methyl 6-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-6-oxohexanoate was dissolved in 3 ml of methanol, mixed with 3 ml of 1 M sodium hydroxide aqueous solution and stirred at room temperature for 4Hours. The reaction solution was concentrated under a reduced pressure, and 1 M hydrochloric acid was added to the residue until it became pH 3.0. After extraction with chloroform and subsequent washing with saturated brine, the organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 237 mg of 6-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-6-oxohexanoic acid as a colorless solid. FP: 559.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure, and 1 M hydrochloric acid
  2. additionwas added to the residue until it
  3. extractionAfter extraction with chloroform
  4. washsubsequent washing with saturated brine
  5. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6170f573da334406a20e3040fa9a8e67
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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