Water → HCID 59299474, compound

HRID 2235262Notes

Reaction equation

HRID 2235262 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]3[CH2:23][CH2:22][N:21]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:20]3=[O:30])=[C:14]([Cl:31])[CH:13]=2)=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[K+].O>C(O)C>[Cl:31][C:14]1[CH:13]=[C:12]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:17]=[CH:16][C:15]=1[CH2:18][CH:19]1[CH2:23][CH2:22][N:21]([CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[C:20]1=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 592993403'-Chloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-2-carboxylic acid ethyl ester

Product 1

HCID 59299474HCID 59299474, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 3′-chloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-2-carboxylic acid ethyl ester (Preparation 81) (287 mg, 0.65 mmol) in ethanol (10 mL) and add KOH (370 mg, 6.5 mmol). Stir at room temperature for 3 days. Pour into water and extract with ether. Acidify the aqueous layer to pH 1. Extract with ether. Dry over sodium sulfate, filter and concentrate to yield 220 mg (82%) of the title compound as a pale yellow solid: Mass spectrum (apci) m/z=410.3 (M−H).

Workup

  1. extractionextract with ether
  2. extractionExtract with ether
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b7724012e06849a59afed1b7a355e021
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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