Hydrochloric Acid → HCID 12002205, compound

HRID 508100Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[C:18]3[S:19][CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)[N:22]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:38][CH2:39][C:40]([O:42]CC)=[O:41].[OH-].[Na+].Cl>C(O)C.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[C:18]3[S:19][CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:31])([F:30])[F:32])=[CH:25][CH:24]=4)[N:22]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:38][CH2:39][C:40]([OH:42])=[O:41]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-[2-fluoro-4-({4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}amino)phenyl]propanoate (0.450 g, 0.720 mmol) in a mixture of ethanol (6 mL) and tetrahydrofuran (15 mL) was added 1 N sodium hydroxide (4.32 mL, 4.32 mmol), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was neutralized with 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from diethyl ether-hexane to give the title compound (0.274 g, yield 64%) as colorless crystals.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record: ord-c39b322411884401a5dfd6a69645afdd
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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