Dimethyl Sulfoxide → HCID 15667301, compound

HRID 847010Notes

Reaction equation

HRID 847010 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].CS(C)=[O:9].[Cl:11][CH2:12][CH2:13][CH2:14][S:15]([NH:18][CH2:19][CH:20](CC(O)C)[CH2:21][O:22][C:23](=[O:43])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:17])=[O:16].C([N:50]([CH2:53][CH3:54])CC)C>ClCCl>[Cl:11][CH2:12][CH2:13][CH2:14][S:15]([NH:18][CH2:19][CH:20]([O:9][C:53]1[CH:54]=[CH:2][O:3][N:50]=1)[CH2:21][O:22][C:23](=[O:43])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14835081HCID 14835081, compound

Product 1

HCID 15667301HCID 15667301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled solution of 0.0645 ml (0.75 mM) of oxalyl chloride in 50 ml of dichloromethane at -78° C., is added 0.106 ml (1.5 mM) of dimethylsulfoxide dropwise and the mixture is stirred for another 5 minutes. To this mixture is added a solution of 285 mg (0.5 mM) of 1-(3-chloropropylsulfonylamino)-2-(2-hydroxypropan-1-yl)-3-octadecylcarbamoyloxypropane m10 in 2 ml of dichloromethane at -70° C. with vigorous stirring. The mixture is allowed to react at -70° C. for 15 minutes and 0.836 ml (6 mM) of triethylamine is added. After allowing the temperature of the reaction mixture to rise to room temperature, the product is isolated with dichloromethane extraction. The dichloromethane layer is washed with 2N aqueous hydrochloric acid, water and saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate and evaporated to obtain crude product of the titled compound III ml.

Workup

  1. customto react at -70° C. for 15 minutes
  2. customto rise to room temperature
  3. washThe dichloromethane layer is washed with 2N aqueous hydrochloric acid, water and saturated aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c845c615330741b3a8834a982cdd1e74
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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