Water → HCID 19801013, compound

HRID 1646660Notes

Reaction equation

HRID 1646660 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6](=[O:37])[NH:7][CH:8]1[CH2:13][CH2:12][C:11]([CH2:15][S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][OH:25])([OH:14])[CH:10]([C:26]2([CH3:34])[O:33][CH:27]2[CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[CH:9]1[O:35][CH3:36])=[O:4].C(N(CC)CC)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47].O>ClCCl>[Cl:1][CH2:2][C:3]([NH:5][C:6](=[O:37])[NH:7][CH:8]1[CH2:13][CH2:12][C:11]([CH2:15][S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][O:25][S:46]([CH3:45])(=[O:48])=[O:47])([OH:14])[CH:10]([C:26]2([CH3:34])[O:33][CH:27]2[CH2:28][CH:29]=[C:30]([CH3:31])[CH3:32])[CH:9]1[O:35][CH3:36])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19801127HCID 19801127, compound

Product 1

HCID 19801013HCID 19801013, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (3 ml) were dissolved 4-(N'-chloroacetylureido)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxycyclohexanol (514 mg) and triethylamine (0.33 ml). To the solution was added dropwise at -20° C. methanesulfonyl chloride (96 μl). The mixture was stirred for 10 minutes, to which was 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 under reduced pressure to leave 4-(N'-chloroacetylureido)-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-methanesulfonyloxymethylbenzyl)thiomethyl-3-methoxycyclohexanol (550 mg; yield 98%) as a colorless powdery product.

Workup

  1. customthe reaction
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-44dc49d16bed4e09bab497e958bf56aa
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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