Sodium Hydroxide → HCID 21310523, compound

HRID 583428Notes

Reaction equation

HRID 583428 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH:9]([N:23]([C:25](=[O:40])[C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)[CH3:24])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C>O1CCCC1.CO>[F:33][C:32]([F:34])([F:35])[C:30]1[CH:31]=[C:26]([CH:27]=[C:28]([C:36]([F:38])([F:37])[F:39])[CH:29]=1)[C:25]([N:23]([CH:9]([CH:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][CH2:7][C:6]([OH:41])=[O:5])[CH3:24])=[O:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54514075HCID 54514075, compound

Product 1

HCID 21310523HCID 21310523, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

45 ml of 1N sodium hydroxide are added to a solution of 15.2 g (27.6 mmol) of 4-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-5,5-diphenyl-pentanoic acid ethyl ester in 160 ml of tetrahydrofuran/methanol (2:1). After 2 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 =0.21; Rt (HPLC)=18.5 min; 1H-NMR (400 MHz, d6 -DMSO, 120° C.) d 7.96 (br, 1H), 7.48-7.18 (m, 12H), 5.43 (br, 1H), 4.31 (d, 1H), 2.55 (br s, 3H). 2.36-2.19 (m, 2H), 1.91 (m, 1H), 1.73 (m, 1H); FAB-MS (M+H)+ =524.

Workup

  1. concentrationAfter 2 hours the reaction mixture is concentrated by evaporation
  2. additiondiluted with water
  3. filtrationThe white precipitate is filtered off
  4. washwashed with water
  5. customdried under a high vacuum at 50° C

Sources & evidence

ORD record
ord-7e220e4e716444d9a4b5bebddcd028fb
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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