Sodium Hydroxide → HCID 67483398, compound

HRID 1816186Notes

Reaction equation

HRID 1816186 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[C:15]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[N:20]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:15]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:29])[F:31])=[CH:25][CH:26]=3)[N:20]=2)=[CH:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[O:39])=[CH:13][CH:12]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67483176HCID 67483176, compound

Product 1

HCID 67483398HCID 67483398, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalyst2×HCID 887MethanolSolvent

Procedure

3-(4-{2-(4-Chlorophenyl)-2-[4-(4-trifluoromethoxyphenyl)thiazol-2-yl]vinyl}benzoylamino)propionic acid methyl ester (14 mg) was dissolved in methanol (5 mL) and 1 N sodium hydroxide (72 μL, 3 equivalents) and 5 drops THF were added and the resulting mixture was stirred at room temperature for 1 hour. More 1 N sodium hydroxide (72 μL, 3 equivalents) and 5 drops THF were added and the resulting mixture was stirred at room temperature for 1 hour and at 50° C. for 1 hour. The mixture was concentrated in vacuo and the residue was added water (5 mL) and 1 N hydrochloric acid was added to pH 2. The solid was filtered off, washed with water and dried in vacuo to afford 6 mg (4%) of the title compound.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour and at 50° C. for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was added water (5 mL) and 1 N hydrochloric acid
  4. additionwas added to pH 2
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5608ed5e4d5d479e9efee5a4c8e5247e
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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