Hydrochloric Acid → 3-[4-(3-Methyl-4'-trifluoromethyl-biphenyl-4-ylmethoxy)-benzoylamino]-propionic acid

HRID 1669263Notes

Reaction equation

C[O:2][C:3](=[O:34])[CH2:4][CH2:5][NH:6][C:7](=[O:33])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:18][C:17]=2[CH3:32])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>C1COCC1>[CH3:32][C:17]1[CH:18]=[C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:27]=2)[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[O:33])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-[4-(3-methyl-4′-trifluoromethyl-biphenyl-4-ylmethoxy)-benzoylamino]-propionic acid methyl ester (0.11 g) and 5M NaOH (1.5 mL) in THF (3 mL) is heated to 70° C. for 12 h. The mixture is acidified with 5M HCl, and extracted with EtOAc. The organics are washed with water and brine, and dried with MgSO4 to yield the title compound. MS (ES): 458 (M+). The structure is also confirmed by 1H NMR.

Workup

extractionextracted with EtOAc
washThe organics are washed with water and brine
dry with materialdried with MgSO4

Sources & evidence

ORD record: ord-606a4a837e8641bb8413e0c83a56d6e4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989457B2

Reaction notes

Loading…