Methyl iodide → HCID 68851119, compound

HRID 1784058Notes

Reaction equation

HRID 1784058 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]([C@@H:18]1[C@@H:20]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@@H:19]1[C:31]([OH:33])=[O:32])=[O:17].[C:34]([O-])([O-])=O.[K+].[K+].IC.[OH-].[Na+]>CN(C=O)C>[CH3:34][O:32][C:31]([C@H:19]1[C@H:20]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@H: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:33]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 68854744HCID 68854744, compound

Product 1

HCID 68851119HCID 68851119, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 90 mg (0.19 mmol) of (1S,2R,3R) 2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-3-(4-methoxy-phenoxymethyl)-cyclopropanecarboxylic acid in 3 ml of DMF was treated with 100 mg of K2CO3 and 0.5 ml ml of iodomethane. The mixture was stirred for 3 hrs and poured into a diluted aqueous solution of NaOH. Extraction with AcOEt, drying of the combined organic phases over Na2SO4, filtration and evaprotation of the solvent gave 90 mg (97%) of (1S,2R,3R) 2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-3-(4-methoxy-phenoxymethyl)-cyclopropanecarboxylicacid methyl ester. Yellow oil. MS: 467 (M+H)+.

Workup

  1. extractionExtraction with AcOEt
  2. dry with materialdrying of the combined organic phases over Na2SO4, filtration and evaprotation of the solvent

Sources & evidence

ORD record
ord-b684634275db4f42b800778664501e6f
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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