4-Toluenesulfonyl chloride → HCID 10786336, compound

HRID 1081195Notes

Reaction equation

HRID 1081195 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:9][C:5]1([CH3:8])[N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:3]([CH2:2][O:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH2:7][O:6]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11053464(R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 10786336HCID 10786336, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10.7 g of t-butyl (R)-4-hydroxymethyl-2,2-dimethyl-3-oxazolidinecarboxylate (J. Org. Chem. 52, 1987, 2361-64) in 107 ml of pyridine is treated with 9.7 g of p-toluenesulphonyl chloride. The reaction mixture is stirred for 17 hours, then taken up in ethyl acetate and washed with water. After drying and evaporation the residue is purified over silica gel with hexane/ethyl acetate (3:1). There are obtained 15.1 g of t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecarboxylate.

Workup

  1. washwashed with water
  2. customAfter drying
  3. customevaporation the residue
  4. customis purified over silica gel with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-9a59b9c89e294327b49785330063ead6
Source dataset
uspto-grants-1996_12
Patent number
US05583133

Reaction notes

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