Water → HCID 71494741, compound

HRID 1487018Notes

Reaction equation

HRID 1487018 reaction equation
[F:1][C:2]([F:32])([F:31])[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][C:24]([F:30])([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[CH2:25][C:24]([F:30])([C:26]([OH:28])=[O:27])[CH2:23]3)=[O:21])[N:14]=2)[CH:4]=[C:3]([C:2]([F:1])([F:32])[F:31])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 71494742HCID 71494742, compound

Product 1

HCID 71494741HCID 71494741, compoundYield 20.6%

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)-3-fluoroazetidine-3-carboxylate (0.01 g, 1.0 eq.) was dissolved in methanol:water (0.2 mL, 1:1), and LiOH (1.0 mg, 1.0 eq) was added. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with 10 mL of water and acidified with dilute HCl to pH 2-3. The aqueous layer was extracted with ethyl acetate (10 mL×3). The combined organic layers were then washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 0.002 g of (Z)-1-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acryloyl)-3-fluoroazetidine-3-carboxylic acid. Yield (20.83%). 1H NMR (400 MHz, CDCL3) δ 8.92 (S, 1H), 8.54 (s, 2H), 8.29 (s, 1H), 7.45-7.42 (d, J=10.4, 1H), 6.00-5.98 (d, J=10.4 Hz, 1H), 3.73 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-65880452a5e346f2ba5bd8208a5fa18b
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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