Sodium Methoxide → HCID 87305197, compound

HRID 547793Notes

Reaction equation

HRID 547793 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:27][C:26](=[O:28])[CH2:25][C@H:24]3[CH2:29][O:30]C(=O)C)=[N:21][CH:22]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[O-].[Na+]>CO.O.[Cl-].[Na+].O>[F:45][C:2]([F:1])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:42])([CH3:43])[C:14]([N:16]([C:17]2[CH:22]=[N:21][C:20]([N:23]3[CH2:27][C:26](=[O:28])[CH2:25][C@H:24]3[CH2:29][OH:30])=[CH:19][C:18]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH3:41])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 131728829HCID 131728829, compound

Product 1

HCID 87305197HCID 87305197, compoundYield 23.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 60 mg (0.094 mmol) (S)-acetic acid 1-(5-{[2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl]-methyl-amino}-4-o-tolyl-pyridin-2-yl)-4-oxo-pyrrolidin-2-ylmethyl ester and a catalytic amount of sodium methylate in 2 ml methanol was stirred at room temperature for 30 min. The reaction mixture was diluted with water and brine and extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 13 mg (23%) of the title compound as a light brown solid.

Workup

  1. extractionextracted with three portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a6f0eda86ce456cb3a41493aab59047
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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