Sodium Hydroxide → HCID 21310519, compound
Reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:39])[CH2:6][CH:7]([N:21]([C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH3:22])[CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.CO>[F:31][C:30]([F:32])([F:33])[C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([C:34]([F:36])([F:35])[F:37])[CH:27]=1)[C:23]([N:21]([CH:7]([CH:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][C:5]([OH:39])=[O:4])[CH3:22])=[O:38]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
25 ml of 1N sodium hydroxide are added to a solution of 7.8 g (15 mmol) of 3-[N-(3,5-bis-trifluoromethyl-benzoyl)-N-methyl-amino]-4,4-diphenyl-butanoic acid methyl ester in 100 ml of tetrahydrofuran/methanol (2:1). After 5 hours the reaction mixture is concentrated by evaporation, diluted with water and rendered acidic with cold 2N hydrochloric acid. The white precipitate is filtered off, then washed with water and dried under a high vacuum at 50° C. The title compound is obtained in the form of a white solid. TLC: methylene chloride/methanol (95:5) Rf =0.14; Rt (HPLC)=19.2 min; 1H-NMR (400 MHz, d6 -DMSO, 150° C.) d 7.96 (br, 1H), 7.42-7.19 (m, 12H), 5.42 (br, 1H), 4.45 (d, 1H), 2.79 (dd, 1H), 2.72 (s, 3H), 2.37 (dd, 1H); FAB-MS (M+H)+ =510.
Workup
- concentrationAfter 5 hours the reaction mixture is concentrated by evaporation
- additiondiluted with water
- filtrationThe white precipitate is filtered off
- washwashed with water
- customdried under a high vacuum at 50° C
Sources & evidence
- ORD record
- ord-e3e91c1f76594fc393709947241a0638
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05929067
Reaction notes
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