Hydrochloric Acid → HCID 67422903, compound

HRID 1172219Notes

Reaction equation

HRID 1172219 reaction equation
C[O:2][C:3]([C@@:5]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:7][C@H:6]1[CH2:8][N:9]1[CH2:14][CH2:13][C:12]([NH:21][C:22](=[O:24])[CH3:23])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:4].[OH-].[Li+].Cl>CO.O>[ClH:31].[C:22]([NH:21][C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:14][N:9]([CH2:8][C@@H:6]2[CH2:7][C@:5]2([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[C:3]([OH:4])=[O:2])[CH2:10][CH2:11]1)(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67424455HCID 67424455, compound

Product 1

HCID 67422903HCID 67422903, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The oxalate salt of (1S,2R)-2-(4-Acetylamino-4-phenyl-piperidin-1-ylmethyl)-1-(3,4-dichlorophenyl)cyclopropanecarboxylic acid methyl ester (10 mmol) was dissolved in methanol (80 mL) and water (20 ml). Lithium hydroxide (50 mmol) was added and the mixture was heated to reflux for 2 h. The mixture was cooled to rt and acidified to pH 3 with concentrated hydrochloric acid and the precipitated product (1S,2R)-2-(4-Acetylamino-4-phenyl-piperidin-1-ylmethyl)-1-(3,4-dichlorophenyl)cyclopropanecarboxylic acid hydrochloride was isolated by filtration and dried in vacuo.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h

Sources & evidence

ORD record
ord-6b6d15043e7243db93f0d3eeea85d4f2
Source dataset
uspto-grants-2010_11
Patent number
US07834008B2

Reaction notes

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