Hydrochloric Acid → HCID 66881522, compound

HRID 1784049Notes

Reaction equation

HRID 1784049 reaction equation
C[O:2][C:3]([CH:5]1[CH:7]([C:8](=[O:24])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])=[CH:12][C:11]=2[F:23])[CH:6]1[C:25](=[O:34])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:25]([CH:6]2[CH:7]([C:8](=[O:24])[NH:9][C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]4=[O:22])=[CH:12][C:11]=3[F:23])[CH:5]2[C:3]([OH:4])=[O:2])=[O:34])=[N:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66882842HCID 66882842, compound

Product 1

HCID 66881522HCID 66881522, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 68 mg (0.14 mmol) of (1RS,2SR,3RS)-2-(5-chloro-pyridin-2-ylcarbamoyl)-3-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid methyl ester (example 114, step 5) in 1.5 ml of THF was treated with 0.2 ml of a 1M aqueous LiOH solution, stirred at RT during 2 hrs and acidified to pH ca. 2 with aqueous HCl. Extraction with AcOEt, drying of the combined organic phases over Na2SO4, filtration and evaporation of the solvent gave 45 mg (68%) of (1RS,2SR,3SR)-2-(5-chloro-pyridin-2-ylcarbamoyl)-3-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopropanecarboxylic acid. Light yellow crystalline. MS: 469 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-7dc9203d9e5b41e8b98b1e3760198f6b
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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