Water → HCID 131717715, compound

HRID 1646651Notes

Reaction equation

HRID 1646651 reaction equation
[Br-:1].[Br:2][C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[CH2:5][CH2:6][SH+:7][CH2:8][C:9]1([OH:27])[CH2:14][CH2:13][CH:12](O)[CH:11]([O:16][CH3:17])[CH:10]1[C:18]1([CH3:26])[O:25][CH:19]1[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].[Cl:32][CH2:33][C:34]([N:36]=[C:37]=[O:38])=[O:35].[OH2:39]>ClCCl>[Br-:2].[Br:1][C:30]1[CH:29]=[CH:28][C:4]([CH2:5][CH2:6][SH+:7][CH2:8][C:9]2([OH:27])[CH2:14][CH2:13][CH:12]([O:39][C:37](=[O:38])[NH:36][C:34](=[O:35])[CH2:33][Cl:32])[CH:11]([O:16][CH3:17])[CH:10]2[C:18]2([CH3:26])[O:25][CH:19]2[CH2:20][CH:21]=[C:22]([CH3:23])[CH3:24])=[CH:3][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78209Chloroacetyl isocyanateHCID 86746497HCID 86746497, compound

Product 1

HCID 131717715HCID 131717715, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-bromobenzyl)methylsulfoniomethyl-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy- 1,4-cyclohexanediol bromide (150 mg) in dichloromethane (2 ml) was added dropwise, under ice-cooling, chloroacetylisocyanate (40 ml), then the mixture was stirred for 30 minutes. To the reaction mixture was added water to suspend the reaction. The product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution, 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 10 g, developing solvent : chloroform-methanol=20:1) to give 1-(4-bromobenzyl)methylsulfoniomethyl-4-(N-chloroacetylcarbamoyloxy)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxycyclohexanol bromide (80 mg: yield 44%).

Workup

  1. temperaturecooling
  2. customthe reaction
  3. extractionThe product was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous saline solution
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent : chloroform-methanol=20:1)

Sources & evidence

ORD record
ord-586515001d09400b86bdb0062bbe1128
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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