p-Toluenesulfonic acid → HCID 118151751, compound

HRID 1506958Notes

Reaction equation

HRID 1506958 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([OH:14])[C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[OH:6].[CH2:16](OC(OCC)C)[CH3:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:1][O:2][C:3]([C@@H:4]1[C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[O:6][CH:16]([CH3:17])[O:14]1)=[O:15]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7765AcetalHCID 90018036HCID 90018036, compound

Product 1

HCID 118151751HCID 118151751, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (MC) was added to (2S,3R)-methyl-3-(2-chlorophenyl)-2,3-dihydroxypropanoate at room temperature. 1,1-Diethoxyethane (8 ml) and p-toluenesulfonic acid (0.27 g) was added and stirred at room temperature. The reaction mixture was quenched with H2O, extracted with MC, washed with H2O, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (3.6 g, 70˜95%).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with MC
  3. washwashed with H2O
  4. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-6f4a26a7920b4b52bbbcb914a4d7e891
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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