Hydrochloric Acid → 5-{[2-(5-Fluoro-2-{[4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)ethyl]amino}pentanoic acid

HRID 1921900Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:7]=1.Cl.O.C(=O)(O)[O-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4.5 g (6.93 mmol) of ethyl 5-{[2-(5-fluoro-2-{[4′-(trifluoromethyl)biphenyl-4-yl]-methoxy}phenyl)ethyl]amino}pentanoate in 90 ml of THF is mixed with 18 ml of half-concentrated hydrochloric acid and heated at 100° C. for 20 min. After cooling, the mixture is added to water and neutralized with saturated sodium bicarbonate solution. It is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is removed in vacuo. The residue is crystallized from ethyl acetate/diethyl ether (1:1). The resulting crystals are filtered off with suction and dried under high vacuum. 2.4 g (4.9 mmol, 71% of theory) of the title compound are obtained.

Workup

temperatureAfter cooling
extractionIt is extracted with ethyl acetate
dry with materialthe organic phase is dried over sodium sulfate
customthe solvent is removed in vacuo
customThe residue is crystallized from ethyl acetate/diethyl ether (1:1)
filtrationThe resulting crystals are filtered off with suction
customdried under high vacuum

Sources & evidence

ORD record: ord-8f8fa02077104518944864a038c12e4f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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