Hydrochloric Acid → 3-[2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy)phenyl)-ethanoylamino]-propionic acid hydrochloride salt

HRID 1296966Notes

Reaction equation

HRID 1296966 reaction equation
C([O:5][C:6](=[O:50])[CH2:7][CH2:8][NH:9][C:10](=[O:49])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[C:39]=2[Cl:48])[CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:13]=1)(C)(C)C.Cl>CCOCC>[ClH:48].[Cl:48][C:39]1[C:40]([C:44]([F:45])([F:46])[F:47])=[CH:41][CH:42]=[CH:43][C:38]=1[CH2:37][N:22]([CH2:23][CH:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:21][CH2:20][CH2:19][O:18][C:14]1[CH:13]=[C:12]([CH2:11][C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:50])=[O:5])=[O:49])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69415730HCID 69415730, compound

Product 1

HCID 99871423-[2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy)phenyl)-ethanoylamino]-propionic acid hydrochloride salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring solution of 3-[2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethanoylamino]-propionic acid tert-butyl ester (110 mg, 0.15 mmol) in Et2O (5 mL) was added 1M HCl in Et2O (0.46 ml, 0.46 mmol). The mixture was stirred at room temperature for 18 hours. Purification by preparative HPLC (YMC, 75×30 mm, 25 ml/min, 40–100% CH3CN:H2O) afforded the desired carboxylic acid. Treatment of the tertiary amine/carboxylic acid with 1 N HCl (Et2O) followed by concentration in vacuo afforded the title compound as a yellow solid (84 mg, 79%). MS(ES) m/e 653.4 (M+).

Workup

  1. customPurification by preparative HPLC (YMC, 75×30 mm, 25 ml/min, 40–100% CH3CN:H2O)

Sources & evidence

ORD record
ord-55102e6e21804a328d61981dda1812b0
Source dataset
uspto-grants-2007_07
Patent number
US07247748B2

Reaction notes

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