Methanol → HCID 66881176, compound

HRID 1784061Notes

Reaction equation

HRID 1784061 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([CH:18]1[CH2:20][CH:19]1[C:21]([OH:23])=[O:22])=[O:17].[CH3:24]O>S(Cl)(Cl)=O>[CH3:24][O:22][C:21]([CH:19]1[CH2:20][CH:18]1[C:16](=[O:17])[NH:15][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:7][C:2]=1[F:1])=[O:23]

Participants

4

Reactant 2

HCID 887MethanolHCID 66882748HCID 66882748, compound

Product 1

HCID 66881176HCID 66881176, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst

Conditions

Temperature
0 °C

Procedure

A stirred suspension of (1RS,2SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid (140 mg) in MeOH (5 ml) was cooled to 0° C. and treated with thionyl chloride (10 drops). The mixture turned immediately into a clear solution. Stirring was continued for 3 hrs at 0° C. Then the reaction mixture was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2−>CH2Cl2/MeOH) to give (1RS,2SR)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid methyl ester (84 mg) as colorless amorphous solid. MS: 353.4 ([M+H]+).

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2−>CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-d491ba9104c64357b1bf083aa7de18f9
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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