Water → HCID 57995481, compound

HRID 385317Notes

Reaction equation

HRID 385317 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[CH:10][C:9]([CH:22]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:23]([O:25]CC)=[O:24])=[CH:8][C:7]=2[N+:32]([O-:34])=[O:33])[CH2:3][CH2:2]1.C1COCC1.O.[Li+].[OH-]>CO>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:16][CH:17]=3)=[CH:10][C:9]([CH:22]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:23]([OH:25])=[O:24])=[CH:8][C:7]=2[N+:32]([O-:34])=[O:33])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57995553HCID 57995553, compound

Product 1

HCID 57995481HCID 57995481, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(6-(cyclopropylmethoxy)-5-nitro-4′-(trifluoromethyl)biphenyl-3-yl)-4-methylpentanoate (100 mg, 0.208 mmol) was taken in a mixture of MeOH; THF:Water (30 ml, 10:10:2) and to it added LiOH (30 mg, 0.7 mmol). The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, it was poured into water (50 ml) and extracted with ethyl acetate (100 ml×2). The ethyl acetate layer was washed with 1N HCl, water and finally brine solution. The organic layer was then distilled off and the crude residue was purified by column chromatography using Ethyl acetate:hexane (1:1) as eluent provided 70 mg of 2-(6-(cyclopropylmethoxy)-5-nitro-4′-(trifluoromethyl)biphenyl-3-yl)-4-methylpentanoic acid. 1H NMR (CDCl3): δ 8.20 (s 1H), 7.40-7.20 (m, 5H), 3.60 (t, 1H), 3.45 (d, 2H), 1.95-2.00 (m, 1H), 1.75-1.80 (m, 1H), 1.45-1.50 (m, 1H), 1.00 (m, 6H), 0.35-0.25 (m, 5H). Mass: (452, M+1, 100%).

Workup

  1. customAfter completion of the reaction, it
  2. extractionextracted with ethyl acetate (100 ml×2)
  3. washThe ethyl acetate layer was washed with 1N HCl, water and finally brine solution
  4. distillationThe organic layer was then distilled off
  5. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-a778318cbce74b7e952046dd3564a788
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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