Sodium Hydroxide → [[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid

HRID 2416647Notes

Reaction equation

HRID 2416647 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:14]([NH:16][CH2:17][C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[O:15])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86592300benzyl [[(2S)-2-[[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]-acetate

Product 1

HCID 69379045[[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzyl [[(2S)-2-[[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]-acetate (10.8 g) in methanol (200 ml) was added 1N aqueous sodium hydroxide solution (22.6 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo, and the residue was treated with aqueous citric acid solution (10%, 100 ml). The resulting white precipitate was collected by filtration, washed with tetrahydrofuran-hexane (1:1, 150 ml), and dried in vacuo to give the title compound (8.25 g) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with aqueous citric acid solution (10%, 100 ml)
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with tetrahydrofuran-hexane (1:1, 150 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f95f9f4c3c234f7e87573da2c6bcdfc6
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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