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

HRID 1266962

反応式

HRID 1266962 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2f8fa56f589e43c6b3b8e47658fbfe98
出典データセット
uspto-grants-2003_04
特許番号
US06551999B1

関連ノート

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