Water → HCID 178440173, 화합물

HRID 248623

반응식

HRID 248623 반응식
[O:1]=[C:2]([C:7]1[N:8]([C:12]2[N:13]=[C:14]([CH2:38][CH2:39][CH3:40])[N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:16]=2[C:17]([O-:19])=[O:18])[CH:9]=[CH:10][CH:11]=1)[C:3]([F:6])([F:5])[F:4].O.C(=O)([O-])[O-].[K+].[K+].SCC(CO)O>CN(C=O)C>[O:1]=[C:2]([C:7]1[N:8]([C:12]2[N:13]=[C:14]([CH2:38][CH2:39][CH3:40])[N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:16]=2[C:17]([OH:19])=[O:18])[CH:9]=[CH:10][CH:11]=1)[C:3]([F:4])([F:5])[F:6]

참가 물질

6

반응물 4

HCID 962Water2회HCID 7291ThioglycerolHCID 11430Potassium Carbonate2회HCID 178440172HCID 178440172, 화합물

생성물 1

HCID 178440173HCID 178440173, 화합물수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-[2-(1-Oxo-2,2,2-trifluoroethyl)-1H-pyrrol-1-yl]-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylate (2.5 g) from Example 13 was dissolved in DMF (45 mL). Water (0.4 mL) followed by potassium carbonate (3.1 g) were added and the reaction mixture stirred at room temperature for 48 hours. Tlc of the reaction mixture showed the reaction to be incomplete. Additional potassium carbonate (0.6 g) and water (0.2 mL) were added and the reaction mixture stirred at room temperature for an another 18 hours. The insoluble materials were removed from the reaction mixture by filtration and washed with DMF A 10% citric acid solution (100 mL) was added slowly to the filtrate and the resulting mixture extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent removed under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to afford 2.06 g (85% yield) of the title compound, mp 185°-188° C., MS (FAB, thioglycerol) 550.3 (M+1).

후처리

  1. additionwere added
  2. customthe reaction
  3. stirringthe reaction mixture stirred at room temperature for an another 18 hours
  4. customThe insoluble materials were removed from the reaction mixture by filtration
  5. washwashed with DMF A 10% citric acid solution (100 mL)
  6. additionwas added slowly to the filtrate
  7. extractionthe resulting mixture extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent removed under reduced pressure
  11. customThe residue was recrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-a94c4ec8e2df434896c25474238912c6
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210211

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