Lauric Acid → (+)-2-{4-(1-Dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine

HRID 274179

反応式

HRID 274179 の反応式
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3].[C:27](O)(=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[C:27]([O:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:8][CH:9]=1)[CH3:3])(=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

参加物

6

反応物 4

HCID 3893Lauric AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

生成物 1

HCID 21468295(+)-2-{4-(1-Dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Into 20 ml of dichloromethane were dissolved 1.78 g (5 millimoles) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)]70 and 1.2 g (6 millimoles) of dodecanic acid, and then 1.4 g of N,N'-dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine were added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the precipitates were filtered off and 200 ml of toluene were added thereto, followed by washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate) to obtain 2.53 g (yield: 94%) of (+)-2-{4-(1-dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine. The physical values are shown in Table-1.

後処理

  1. customAfter completion of the reaction
  2. filtrationthe precipitates were filtered off
  3. addition200 ml of toluene were added
  4. washby washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order
  5. dry with materialAfter the organic phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate)

出典と根拠

ORDレコード
ord-2026f0e84e994620be221f3c645de7d2
出典データセット
uspto-grants-1995_02
特許番号
US05389293

関連ノート

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