Hydrochloric Acid → 2-Ethyl 3-[3-[4-(trifluoromethyl)benzylamino-methyl]-4-methoxyphenyl]propanoic acid hydrochloride

HRID 1826089Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzylaminomethyl]-4-methoxyphenyl]propanoate (90.2 mg, 0.213 mmol), methanol (2 mL) and 2.5 mol/L aqueous solution of sodium hydroxide (2 mL) was stirred for 5 hours under heating at 60° C. After cooling, ice water (20 mL) was added and the mixture was made acidic with 1 mol/L hydrochloric acid, which was then saturated with sodium chloride and extracted with ethyl acetate. The extracte was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=10:1 v/v) to afford 78.0 mg (85%) of the title compound as a brown oil.

Workup

temperatureAfter cooling
extractionsaturated with sodium chloride and extracted with ethyl acetate
washThe extracte was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=10:1 v/v)

Sources & evidence

ORD record: ord-30d74dc7e27b44578217ae3f4a319d93
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049342B2

Reaction notes

Loading…