Hydrochloric Acid → HCID 66882141, compound

HRID 1784045Notes

Reaction equation

HRID 1784045 reaction equation
C([O:3][C:4]([CH:6]1[CH:8]([C:9](=[O:25])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])=[CH:13][C:12]=2[F:24])[CH:7]1[C:26](=[O:35])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[O:5])C.[Li+].[OH-].Cl>C1COCC1>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:26]([CH:7]2[CH:8]([C:9](=[O:25])[NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]4=[O:23])=[CH:13][C:12]=3[F:24])[CH:6]2[C:4]([OH:5])=[O:3])=[O:35])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66880761HCID 66880761, compound

Product 1

HCID 66882141HCID 66882141, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 80 mg (0.16 mmol) of (1RS,2RS,3SR)-2-(4-chloro-phenylcarbamoyl)-3-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid ethyl ester (example 68) in a mixture of 10 ml of THF and 10 ml of a 1M aqueous LiOH-solution was stirred during 2 hrs at room temperature. The mixture was poured into 50 ml of a aqueous HCl-solution (0.5 M), extracted with AcOEt and the combined organic phases were dried over Na2SO4. Evaporation of the solvent gave 65 mg (86%) of the title compound. Off-white solid. MS: 468 (M−H)−.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-576a1ea47e45462dad2e5c13b42a3598
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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