4-Toluenesulfonyl chloride → HCID 15549882, compound

HRID 1082186Notes

Reaction equation

HRID 1082186 reaction equation
[CH:1]1([C@@H:4]([OH:11])[C@H:5]([OH:10])[C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[CH:1]1([C@@H:4]([OH:11])[C@H:5]([O:10][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[C:6]([O:8][CH3:9])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 15549881HCID 15549881, compound

Product 1

HCID 15549882HCID 15549882, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, a solution of 4.22 g of methyl (2S,3R)-3-cyclopropyl-2,3-dihydroxypropionate in 140 ml of methylene chloride is cooled to -3° C. Then, 4.00 g of triethylamine and 5.17 g of p-toluenesulfonyl chloride are added to the mixture successively. The mixture is stirred for 3 days. Then, the solvent is removed in vacuo. The residue is poured into a mixture of ethyl acetate and water. The organic layer is washed with brine and dried. The solvent is removed in vacuo. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=1:3) to give 6.54 g of methyl (2S,3R)-3-cyclopropyl-3-hydroxy-2-(p-toluenesulfonyloxy)propionate

Workup

  1. customThen, the solvent is removed in vacuo
  2. additionThe residue is poured into a mixture of ethyl acetate and water
  3. washThe organic layer is washed with brine
  4. customdried
  5. customThe solvent is removed in vacuo
  6. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-a26324051b854a1b8ff2a33482f40546
Source dataset
uspto-grants-1996_12
Patent number
US05589502

Reaction notes

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