Hydrochloric Acid → {6-Benzyloxy-2'-[(benzyloxycarbonyl-ethyl-amino)-methyl]-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid

HRID 563664Notes

Reaction equation

C([O:3][C:4](=[O:44])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=2[CH2:30][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:32][CH3:33])[C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:11]=1)C.[Li+].[OH-].Cl>CO>[CH2:13]([O:12][C:9]1[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][C:21]=2[CH2:30][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35])[CH2:32][CH3:33])=[CH:7][C:6]([CH2:5][C:4]([OH:44])=[O:3])=[CH:11][CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of {6-benzyloxy-2′-[(benzyloxycarbonyl-ethyl-amino)-methyl]-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester (0.050 g, 0.08 mmol) in MeOH (3 mL) was added 1N aqueous LiOH (1 mL), and the reaction was stirred at 65° C. overnight. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound. M+H is 578.

Workup

extractionextracted with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-b0ffcdf6812340618b7fd41bdb12cbea
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067445B2

Reaction notes

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