Methanethiol → HCID 19801122, compound

HRID 1646636Notes

Reaction equation

HRID 1646636 reaction equation
[CH3:1][C:2]([CH3:27])=[CH:3][CH2:4][C@@H:5]1[O:7][C@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([O:17][C:18]([NH:20]C(CCl)=O)=[O:19])[C@H:10]1[O:25][CH3:26])[CH3:8].[CH3:28][SH:29].[Na]>C(O)C>[C:18]([O:17][CH:11]1[CH2:12][CH2:13][C:14]([CH2:15][S:29][CH3:28])([OH:16])[CH:9]([C:6]2([CH3:8])[O:7][CH:5]2[CH2:4][CH:3]=[C:2]([CH3:27])[CH3:1])[CH:10]1[O:25][CH3:26])(=[O:19])[NH2:20]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 5360545SodiumHCID 14942883O-chloroacetylcarbamoyl fumagillol

Product 1

HCID 19801122HCID 19801122, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of O-chloroacetylcarbamoyl fumagillol (209 mg) in ethanol (2 ml) was added a 15% aqueous solution of methanethiol.sodium salt (500 μl), and the mixture was stirred for one hour at room temperatures. The reaction mixture was concentrated, to which was added ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: hexane-ethyl acetate=2:1) to afford 4-O-carbamoyl-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl) -3-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (136 mg: yield 70%) as colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated, to which
  2. additionwas added ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent: hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4a791f36f8db45a59c3c7a5f74d9f043
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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