Sodium Hydroxide → HCID 10116357, compound

HRID 2230898Notes

Reaction equation

HRID 2230898 reaction equation
C([O:3][C:4](=[O:37])[CH:5]([NH:18][C:19]([C:21]1([NH:26][C:27](=[O:36])[CH:28]([S:32]C(=O)C)[CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])[CH2:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)C.[OH-].[Na+]>CO.O>[SH:32][CH:28]([CH:29]([CH3:31])[CH3:30])[C:27]([NH:26][C:21]1([C:19]([NH:18][CH:5]([CH2:6][C:7]2[S:8][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[C:4]([OH:37])=[O:3])=[O:20])[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22956154HCID 22956154, compound

Product 1

HCID 10116357HCID 10116357, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

55 mg (0.101 mmol) of 2-{[1-(2-Acetylthio-3-methyl-butanoylamino)-cyclopentanecarbonyl]-amino}3-(5-phenyl-thien-2-yl)-propionic acid ethyl ester is dissolved in 2 mL of MeOH. 0.41 mL of 1N NaOH is added, and the solution is stirred at room temperature for 3 h. The reaction mixture is diluted with water, and MeOH is removed in vacuo. The residue is partitioned between water and Et2O. The aqueous phase is extracted twice with Et2O, acidified with 0.41 mL of 1N HCl, and then extracted with EtOAc. The EtOAc phase is concentrated to furnish the product; mp 154-155° C.

Workup

  1. customis removed in vacuo
  2. customThe residue is partitioned between water and Et2O
  3. extractionThe aqueous phase is extracted twice with Et2O
  4. extractionextracted with EtOAc
  5. concentrationThe EtOAc phase is concentrated
  6. customto furnish the product

Sources & evidence

ORD record
ord-4b270799f9a543298931fe18c0382fb3
Source dataset
uspto-grants-2002_07
Patent number
US06426354B1

Reaction notes

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