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

HRID 1650625
ノート
印刷プレビュー

反応式

HRID 1650625 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d90a48f9249840138f3c8b7c2d4789c1
出典データセット
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04925649

反応ノート

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