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

HRID 1650625Notes

Reaction equation

HRID 1650625 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d90a48f9249840138f3c8b7c2d4789c1
Source dataset
uspto-grants-1990_05
Patent number
US04925649

Reaction notes

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