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Dicyclohexylcarbodiimide → 1-octanoyl-2-[3-(m-iodophenyl)propanoyl]-3-O-trityl-rac-glycerol

HRID 1650625
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HRID 1650625 반응식
[C:1]([O:10][CH2:11][CH:12]([CH2:14][O:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[OH:13])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[I:35][C:36]1[CH:37]=[C:38]([CH2:42][CH2:43][C:44](O)=[O:45])[CH:39]=[CH:40][CH:41]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:10][CH2:11][CH:12]([CH2:14][O:15][C:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[O:13][C:44](=[O:45])[CH2:43][CH2:42][C:38]1[CH:39]=[CH:40][CH:41]=[C:36]([I:35])[CH:37]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 38702213-(3-Iodophenyl)propionic acidHCID 147716501-octanoyl-3-O-trityl-rac-glycerol

생성물 1

HCID 147716511-octanoyl-2-[3-(m-iodophenyl)propanoyl]-3-O-trityl-rac-glycerol수율 73.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매
2회

실험 절차

1-Octanoyl-3-O-trityl-rac-glycerol (414 mg, 0.90 mmol), 3-(m-iodophenyl)propanoic acid (250 mg, 0.91 mmol) and DMAP were dissolved in CH2Cl2 (8.3 ml). DCC (206 mg, 1.00 mmol) was added and the mixture was stirred overnight. The mixture was then diluted with CH2Cl2. The organic and aqueous phases were separated and washed twice with 1 N HCl, once with saturated NaHCO3, once with H2O, and once with brine. The organic layer was then dried over MgSO4 and evaporated. Purification by chromatography on 12 g silica gel and with a hexanes:ethyl acetate (8:1) solvent yielded pure compound 44, 1-octanoyl-2-[3-(m-iodophenyl)propanoyl]-3-O-trityl-rac-glycerol (473.5 mg. 73% Yield).

후처리

  1. customThe organic and aqueous phases were separated
  2. washwashed twice with 1 N HCl, once with saturated NaHCO3, once with H2O
  3. dry with materialThe organic layer was then dried over MgSO4
  4. customevaporated
  5. customPurification by chromatography on 12 g silica gel

출처 및 근거

ORD 기록
ord-d90a48f9249840138f3c8b7c2d4789c1
출처 데이터셋
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04925649

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