Water → HCID 19801059, compound

HRID 1646656Notes

Reaction equation

HRID 1646656 reaction equation
[Cl:1][CH2:2][C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[CH2:5][S:6][CH2:7][C:8]1([OH:26])[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([O:15][CH3:16])[CH:9]1[C:17]1([CH3:25])[O:24][CH:18]1[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].[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:14][CH:11]1[CH2:12][CH2:13][C:8]([CH2:7][S:6][CH2:5][C:4]2[CH:27]=[CH:28][CH:29]=[CH:30][C:3]=2[CH2:2][Cl:1])([OH:26])[CH:9]([C:17]2([CH3:25])[O:24][CH:18]2[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH:10]1[O:15][CH3:16])=[O:37])=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 78209Chloroacetyl isocyanateHCID 19801120HCID 19801120, compound

Product 1

HCID 19801059HCID 19801059, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (1.5 ml) was dissolved 1-(2-chloromethylbenzyl)thiomethyl-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1,4-cyclohexanediol (300 mg). To the solution was added dropwise, under ice-cooling, chloroacetylisocyanate (84 μl). The mixture was stirred for 15 minutes, to which was added water to suspend the reaction. The product was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous solution of sodium chloride, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent : methyl acetate - hexane=1:2) to give 4-(N-chloroacetylcarbamoyloxy)-1-(2-chloromethylbenzyl)thiomethyl-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxycyclohexanol (302 mg: yield 79%) as colorless powder.

Workup

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

Sources & evidence

ORD record
ord-6ba5fedc76da461784e15748737f2a9d
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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