p-Toluenesulfonic acid → HCID 118140878, compound

HRID 1506953Notes

Reaction equation

HRID 1506953 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].CO[C:18](OC)([CH3:20])[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[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][C:18]([CH3:20])([CH3:19])[O:14]1)=[O:15]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 90018918HCID 90018918, compound

Product 1

HCID 118140878HCID 118140878, compoundYield 82.4%

Conditions

Temperature
0 °C

Procedure

Dichloromethane(DMC) was added to (2S,3R)-methyl-3-(2-chlorophenyl)-2,3-dihydroxypropanoate (24.4 g, Preparation example 25) and cooled to 0° C. 2,2-Dimethoxypropane (26 ml, 211.77 mmol) and p-toluenesulfonic acid (2 g, 10.58 mmol) was added and stirred at room temperature. The reaction mixture was quenched with H2O, extracted with DCM, washed with H2O, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (23.6 g, 70˜95%).

Workup

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

Sources & evidence

ORD record
ord-a4f83bf7b85f44aba3f4a0df2f6d4024
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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