Hexane → HCID 54509325, compound

HRID 989998Notes

Reaction equation

HRID 989998 reaction equation
C(=O)(OC(Cl)(Cl)Cl)[O:2][C:3](Cl)(Cl)[Cl:4].[CH2:13]([O:20][C:21]([NH:23][C@H:24]([C:28]([O:30][CH2:31][CH:32]([CH2:34][O:35][C:36](=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[OH:33])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.CCCCCC>ClCCl>[CH2:13]([O:20][C:21]([NH:23][C@H:24]([C:28]([O:30][CH2:31][CH:32]([O:33][C:3]([Cl:4])=[O:2])[CH2:34][O:35][C:36](=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 94429TriphosgeneHCID 23387482HCID 23387482, compound2×

Product 1

HCID 54509325HCID 54509325, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(trichloromethyl) carbonate (160 mg; 0.54 mmol) was added with stirring to a solution of 1-(N-benzyloxycarbonyl-L-valyl)-3-stearoylglycerol; 1-(N-benzyloxycarbonyl-L-valyloxy)-3-stearoyloxy-2-propanol; preparative example 4; (660 mg; 1.12 mmol) and triethylamine (200 mg; 2.0 mmol) in dichloromethane (5 ml) at room temperature. After 1 h, n-hexane (10 ml) was added and the precipitated triethylamine hydrochloride was filtered off through a short column of silica gel, the product eluted with a further amount of n-hexane, and the solvent evaporated in vacuum to yield 650 mg (89%) of the title compound.

Workup

  1. customat room temperature
  2. filtrationthe precipitated triethylamine hydrochloride was filtered off through a short column of silica gel
  3. washthe product eluted with a further amount of n-hexane
  4. customthe solvent evaporated in vacuum

Sources & evidence

ORD record
ord-b661f269ca6b485f9aff1fc9d4589109
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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