Dichloromethane → HCID 14834976, compound

HRID 846972Notes

Reaction equation

HRID 846972 reaction equation
C([O:8][CH2:9][CH:10]([O:34][CH3:35])[CH2:11][S:12][C:13](=[O:33])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])C1C=CC=CC=1.C[Si](I)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+].ClCCl>C(#N)C>[CH2:15]([NH:14][C:13]([S:12][CH2:11][CH:10]([O:34][CH3:35])[CH2:9][OH:8])=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 198842443-Benzyloxy-2-methoxy-1-octadecylcarbamoylthiopropane

Product 1

HCID 14834976HCID 14834976, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.02 g (2 mM) of 3-benzyloxy-2-methoxy-1-octadcylcarbamoylthiopropane VI a6 in 80 ml of acetonitrile is added 0.4 ml (2.81 mM) of trimethylsilyl iodide with ice-cooling and the mixture is allowed to stand at room temperature for 15 hours. To the reaction mixture is added 50 ml of 10% aqueous solution of sodium thiosulfate and the product is isolated with dichloromethane extraction. The dichloromethane layer is washed with water, dried, and evaporated. The residue is purified by column chromatography on silica gel using a n-hexane-ethyl acetate (2:1) mixture as an eluent to give 480 mg (1.15 mM) of the titled compound, 3-octadecylcarbamoylthio-2-methoxypropylalcohol V a6 as a solid in 57% yield.

Workup

  1. temperaturecooling
  2. washThe dichloromethane layer is washed with water
  3. customdried
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel using a n-hexane-ethyl acetate (2:1) mixture as an eluent

Sources & evidence

ORD record
ord-4488ff6031fa4abfb8157bb874b57be3
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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