Water → 5-benzyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylic acid

HRID 219567

반응식

HRID 219567 반응식
[CH2:1]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[N:11]=[N:10][C:9]=1[C:20]([O:22]C)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O>CCO>[CH2:1]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[N:11]=[N:10][C:9]=1[C:20]([OH:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68649205Methyl 5-benzyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate

생성물 1

HCID 596042285-benzyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Methyl 5-benzyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate obtained in Step 1 as described above was dissolved in EtOH and NaOH (8.10 ml; 5 M; 40.48 mmol; 5 eq.) was added, the mixture was stirred overnight at room temperature. Water (30 mL) was added and the aqueous phase was washed with Et2O (2×30 mL). The aqueous layer was acidified to pH 2 with HCl 5 N and extracted with EtOAc (2×50 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated under vacuum affording the title compound as a yellow oil. It was taken up in petroleum ether and it was sonicated. The suspension was filtered off, affording Intermediate 24 as a beige solid. 1H-NMR (DMSO-d6, 300 MHz) δ 13.43 (br s, 1H), 7.74-7.69 (m, 1H), 7.64-7.58 (m, 1H), 7.53-7.42 (m, 2H), 7.22-7.17 (m, 3H), 6.83-6.72 (m, 2H), 4.38 (s, 2H). LC/MS (Method B): 298.2 (M+H)+. HPLC (Method A) Rt 3.60 min (Purity: 92.7%).

후처리

  1. washthe aqueous phase was washed with Et2O (2×30 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-ee0e489745374110b519ad620b700ca9
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202856B2

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