Dicyclohexylcarbodiimide → 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine

HRID 1728262노트

반응식

HRID 1728262 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[CH:35][C:34]([OH:37])=[CH:33][N:32]=2)=[CH:27][CH:26]=1)[CH2:17][CH3:18].[C:38](O)(=[O:46])[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH3:45]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[CH:35][C:34]([O:37][C:38](=[O:46])[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH3:45])=[CH:33][N:32]=2)=[CH:27][CH:26]=1)[CH2:17][CH3:18]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 5282715cis-beta-Octenoic acidHCID 190171892-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine

생성물 1

HCID 676342202-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine수율 83.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

0.8 g of N,N'-dicyclohexylcarbodiimide was added within 5 minutes while stirring to a solution of 1.0 g of 2-[4-(5[propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine, 0.4 g of (Z)-3-octenoic acid and 0.05 g of 4-(dimethylamino)pyridine in 30 ml of dichloromethane. The reaction mixture was stirred overnight, then filtered and the filtrate was washed with saturated sodium bicarbonate solution and with water and concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) and two-fold recrystallization of the thin-layer chromatographically pure fractions gave 1.0 g of 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine.

후처리

  1. filtrationfiltered
  2. washthe filtrate was washed with saturated sodium bicarbonate solution and with water
  3. concentrationconcentrated
  4. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) and two-fold recrystallization of the thin-layer chromatographically pure fractions

출처 및 근거

ORD 기록
ord-40373b5c592c4b369fb23c202e4c595d
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05326497

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