Hydrochloric Acid → HCID 58288237, compound

HRID 1476141Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

300 mg (0.633 mmol) of ethyl 3-(3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-4-fluorophenyl)-2-methylpropanoate (diastereomer mixture) were dissolved in a mixture of in each case 1.0 ml of methanol, THF and water, and 265.5 mg (6.33 mmol) of lithium hydroxide were added at 0° C. The mixture was stirred initially at 0° C. for 1 h and then at RT for 1 h. The solution was then diluted with water and acidified with 1 N hydrochloric acid (pH about 2). The aqueous phase was extracted three times with diethyl ether and once with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. This gave 294 mg (99.7% of theory) of the title compound as a mixture of four diastereomers.

Workup

additionwere added at 0° C
waitat RT for 1 h
extractionThe aqueous phase was extracted three times with diethyl ether
dry with materialThe combined organic phases were dried over sodium sulphate
concentrationconcentrated under reduced pressure
additionThis gave 294 mg (99.7% of theory) of the title compound as a mixture of four diastereomers

Sources & evidence

ORD record: ord-7c872505ba4f48bc9f9d4639cfb0e419
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018414B2

Reaction notes

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