Sodium Hydroxide → HCID 70129737, compound

HRID 1251885Notes

Reaction equation

HRID 1251885 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:33]=[CH:32][C:19]([C:20]([NH:22][C@@H:23]([CH2:28][CH2:29][S:30][CH3:31])[C:24]([O:26]C)=[O:25])=[O:21])=[C:18]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH:17]=2)[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:33]=[CH:32][C:19]([C:20]([NH:22][C@@H:23]([CH2:28][CH2:29][S:30][CH3:31])[C:24]([OH:26])=[O:25])=[O:21])=[C:18]([C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)[CH:17]=2)[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585137HCID 86585137, compound

Product 1

HCID 70129737HCID 70129737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (2S)-2-{4-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenyl)benzoylamino}-4-methylsulfanylbutyrate (0.037 g; 0.061 mmol) in methanol (3 ml) was treated with 2N aqueous sodium hydroxide solution (0.32 ml) and the mixture stirred at ambient temperature for 2 hours. After evaporation of the methanol, the aqueous residue was acidified to pH 7.5 with 6N HCl and purified on reverse phase silica eluting with a gradient of 50-60% methanol ammonium carbonate buffer (2 g/l, pH 7). The appropriate fractions were concentrated and freeze-dried to give the title compound as a solid.

Workup

  1. customAfter evaporation of the methanol
  2. custompurified on reverse phase silica eluting with a gradient of 50-60% methanol ammonium carbonate buffer (2 g/l, pH 7)
  3. concentrationThe appropriate fractions were concentrated
  4. customfreeze-dried

Sources & evidence

ORD record
ord-a1112c29ec4247eba0062567943e3183
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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