Water → 1,1-Dimethylethyl 2-(4-(4-fluorophenyl)-1-piperazinyl)-2-oxo-1-(phenylmethyl)ethylcarbamate

HRID 1266962

반응식

HRID 1266962 반응식
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[N+](C1C=CC([O:32][C:33](=O)[C@H:34]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=CC=1)([O-])=O.O>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:33](=[O:32])[CH:34]([NH:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42])[CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 111308Boc-Phe-ONpHCID 162119161-(4-Fluorophenyl)piperazine dihydrochloride

생성물 1

HCID 538047351,1-Dimethylethyl 2-(4-(4-fluorophenyl)-1-piperazinyl)-2-oxo-1-(phenylmethyl)ethylcarbamate수율 92.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-(4-fluorophenyl)piperazine dihydrochloride (2.53 g, 10 mmol) in N,N-dimethylformamide (40 ml) were added triethylamine (2.8 ml, 20 mmol) and N-tert butoxycarbonylphenylalanine p-nitrophenyl ester (2.65 g, 10 mmol) in the order mentioned, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into cold water and extracted with ethyl acetate. The extract was washed with 1 w/v % aqueous ammonia, saturated brine, 0.1N hydrochloric acid, saturated brine, saturated aqueous sodium hydrogencarbonate solution, and saturated brine in the order mentioned, and the organic layer was dried over anhydrous magnesium sulfate and further concentrated under reduced pressure. The residue was purified by silica gel column chromatography using chloroform-methanol (50:1, v/v) to give 1,1-dimethylethyl 2-(4-(4-fluorophenyl)-1-piperazinyl)-2-oxo-1-(phenylmethyl)ethylcarbamate (2.7 g, 92.2%) as colorless oil.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1 w/v % aqueous ammonia, saturated brine, 0.1N hydrochloric acid, saturated brine, saturated aqueous sodium hydrogencarbonate solution, and saturated brine in the order
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationfurther concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2f8fa56f589e43c6b3b8e47658fbfe98
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06551999B1

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