Water → HCID 19801127, compound

HRID 1646659Notes

Reaction equation

HRID 1646659 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][C:5]([CH2:9][S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][OH:19])([OH:8])[CH:4]([C:20]2([CH3:28])[O:27][CH:21]2[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:3]1[O:29][CH3:30].[Cl:31][CH2:32][C:33]([N:35]=[C:36]=[O:37])=[O:34].O>ClCCl>[Cl:31][CH2:32][C:33]([NH:35][C:36](=[O:37])[NH:1][CH:2]1[CH2:7][CH2:6][C:5]([CH2:9][S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][OH:19])([OH:8])[CH:4]([C:20]2([CH3:28])[O:27][CH:21]2[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:3]1[O:29][CH3:30])=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 78209Chloroacetyl isocyanateHCID 19801049HCID 19801049, compound

Product 1

HCID 19801127HCID 19801127, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (20 ml) was dissolved 4-amino-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxycyclohexanol (629 mg). To the solution was added dropwise, under ice-cooling, chloroacetyl isocyanate (0.22 ml). The mixture was stirred for 10 minutes, to which was then added water to suspend the reaction. The reaction product was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous solution of sodium chloride and, then, dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent: ethyl acetate - hexane=3:2) to afford 4-(N'-chloroacetylureido)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxycyclohexanol (514 mg: yield 64%) as a colorless powdery product.

Workup

  1. additionTo the solution was added dropwise, under ice-
  2. temperaturecooling
  3. customthe reaction
  4. extractionThe reaction product was extracted with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent: ethyl acetate - hexane=3:2)

Sources & evidence

ORD record
ord-294e88f49c9c416786542ff3c87c667c
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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