Water → HCID 10134854, compound

HRID 1071856Notes

Reaction equation

HRID 1071856 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C@H:14]1[CH2:28][O:27][C:17]2[CH:18]=[CH:19][C:20]3[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=3[C:16]=2[O:15]1.O>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[CH2:28][O:27][C:17]3[CH:18]=[CH:19][C:20]4[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=4[C:16]=3[O:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 69744945HCID 69744945, compound

Product 1

HCID 10134854HCID 10134854, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (0.60 g, 3.15 mmole) was added to solution of (2S)-2-(hydroxymethyl)-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-7-one (0.41 g, 1.75 mmole) in 50 mL of pyridine. The solution was stirred at room temperature overnight under nitrogen. Water was added to quench the excess tosyl chloride and the solvent was removed in vacuum and replaced with methylene chloride. The solution was washed with 2N aqueous HCl, with saturated aqueous sodium bicarbonate, and with saturated brine, and dried over magnesium sulfate. Filtration, evaporation in vacuum and column chromatography on silica gel with 3% methanol/methylene chloride as eluant gave 0.36 g (54%) of the (R)-enantiomer of the title compound as a yellow solid, m.p. 190-191° C.

Workup

  1. customto quench the excess tosyl chloride
  2. customthe solvent was removed in vacuum
  3. washThe solution was washed with 2N aqueous HCl, with saturated aqueous sodium bicarbonate
  4. dry with materialwith saturated brine, and dried over magnesium sulfate
  5. filtrationFiltration, evaporation in vacuum and column chromatography on silica gel with 3% methanol/methylene chloride as eluant

Sources & evidence

ORD record
ord-c061686132b6473cb5626961bb61cb2f
Source dataset
uspto-grants-2005_06
Patent number
US06906206B2

Reaction notes

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