Water → HCID 71494738, compound

HRID 1486998Notes

Reaction equation

HRID 1486998 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([N:22]3[CH2:25][CH:24]([C:26]([O:28]C)=[O:27])[CH2:23]3)=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.[Li+].[OH-]>CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([N:22]3[CH2:23][CH:24]([C:26]([OH:28])=[O:27])[CH2:25]3)=[O:21])[N:14]=2)[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 89402004HCID 89402004, compound

Product 1

HCID 71494738HCID 71494738, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-methyl 1-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)azetidine-3-carboxylate (0.1 g, 1.0 eq.) was dissolved in methanol:water (10 mL, 1:1). LiOH (0.010 g, 1.0 eq.) was added. The reaction mixture was stirred at room temperature for 1-2 h. The reaction mixture was quenched with 10 mL water and acidified with dilute HCl until pH=2-3. The aqueous layer was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford 0.060 g of (Z)-1-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)azetidine-3-carboxylic acid (62.5% yield). 1H NMR (400 MHz, DMSO) δ=9.38 (s, 1H), 8.54 (s, 2H), 8.29 (s, 1H), 7.40-7.42 (d, J=10.4 Hz, 1H), 5.93-5.96 (d, J=10.4 Hz, 1H), 4.23-4.27 (m, 2H), 4.12-4.16 (m, 3H). LCMS calcd. for C17H13F6N4O3 [M+H]+: 435.29. Found: 435.14, at 2.55 min retention time.

Workup

  1. customThe reaction mixture was quenched with 10 mL water
  2. extractionThe aqueous layer was extracted with ethyl acetate (10 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0b15fa9c74049a19674662b1b46c74b
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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