Hydrochloric Acid → Tert-butyl 5-(4-tert-butoxycarbonyl-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole-2-carboxylate

HRID 589645

반응식

HRID 589645 반응식
[C:1]([O:5][C:6](=[O:52])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][C:15]([CH:28]([N:36]=C(C2C=CC=CC=2)C2C=CC=CC=2)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:51])([CH3:4])([CH3:3])[CH3:2].Cl.O>CC(C)=O>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][C:15]([C:20]3[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=3)([C:16]([F:18])([F:17])[F:19])[CH:28]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[N:36]=2)=[CH:9][C:8]=1[CH3:51])=[O:52])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 866960024-[3-[(Benzhydrylidene-amino)-tert-butoxycarbonyl-methyl]-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butyryl]-2-methyl-benzoic acid tert-butyl ester

생성물 1

HCID 86696003Tert-butyl 5-(4-tert-butoxycarbonyl-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole-2-carboxylate수율 76.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Similarly, the reaction was carried out under similar conditions: To a solution of 4-[3-[(Benzhydrylidene-amino)-tert-butoxycarbonyl-methyl]-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-butyryl]-2-methyl-benzoic acid tert-butyl ester (426 mg, one diastereoisomer, obtained in example P12) in acetone (12 mL) was added hydrochloric acid (6 mL, 10%) and the solution was stirred at ambient temperature for 3 hours. Water was then added and the reaction mixture was extracted with ethylacetate and the combined organic fractions were dried over sodium sulfate. The crude product was purified by flash chromatography (0% to 05% dichloromethane in heptane) to afford tert-butyl 5-(4-tert-butoxycarbonyl-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole-2-carboxylate (248 mg) as a white solid. 19F NMR (376 MHz, CDCl3) δ −75.20 ppm (1 diastereoisomers). Chiral HPLC analysis (Chiralpack AS-RH, acetonitrile:water:methanol=55:5:40, 1 ml/min, retention time 22.87 minutes (minor enantiomer) and 25.52 minutes (major isomer) indicated that the reaction proceeded with little enantioselectivity.

후처리

  1. extractionthe reaction mixture was extracted with ethylacetate
  2. dry with materialthe combined organic fractions were dried over sodium sulfate
  3. customThe crude product was purified by flash chromatography (0% to 05% dichloromethane in heptane)

출처 및 근거

ORD 기록
ord-b8473c29f9d1423da78725445f0a03b4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233920B2

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