Dimethyl Sulfate → HCID 66881688, compound

HRID 1784051Notes

Reaction equation

HRID 1784051 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([C:9](=[O:26])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]3=[O:24])=[CH:13][C:12]=2[F:25])[CH:7]1[C:27](=[O:36])[NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)=[O:5])[CH3:2].[C:37](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([C:9](=[O:26])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:37])=[CH:19][C:18]3=[O:24])=[CH:13][C:12]=2[F:25])[CH:7]1[C:27](=[O:36])[NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 66882346HCID 66882346, compound

Product 1

HCID 66881688HCID 66881688, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 35 mg (0.07 mmol) of (1SR,2RS,3SR)-2-(4-chloro-phenylcarbamoyl)-3-[2-fluoro-4-(4-hydroxy-2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid ethyl ester (example 142, step 2) in 5 ml of acetone was treated with 94 mg (0.6 mmol) of potassium carbonate and 8 ul (0.08 mmol) of dimethylsulfate. The mixture was stirred 2 hrs at RT and filtered. Evaporation of the solvent and chromatography on silica gel with AcOEt/methanol 95:5 gave 5 mg (13%) of (1SR,2RS,3SR)-2-(4-chloro-phenylcarbamoyl)-3-[2-fluoro-4-(4-methoxy-2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid ethyl ester. Off-white solid. 526 (M−H)−.

Workup

  1. filtrationfiltered
  2. customEvaporation of the solvent and chromatography on silica gel with AcOEt/methanol 95:5

Sources & evidence

ORD record
ord-71f674dad4e143ab951272dcf324cfbc
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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