p-Toluenesulfonic acid → HCID 53731885, compound

HRID 439581Notes

Reaction equation

HRID 439581 reaction equation
C([O:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N:20]([CH3:22])[CH3:21])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)C.[C:23]1(C)[CH:28]=[CH:27]C(S(O)(=O)=O)=[CH:25][CH:24]=1>C(O)C1C=CC=CC=1.C1C=CC=CC=1>[OH:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N:20]([CH3:21])[CH3:22])[CH:13]=1)[C:6]([O:8][CH2:9][C:10]1[CH:27]=[CH:28][CH:23]=[CH:24][CH:25]=1)=[O:7]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54067989HCID 54067989, compound

Product 1

HCID 53731885HCID 53731885, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 244Benzyl AlcoholSolvent

Procedure

To a solution of ethyl (R)-2-acetoxy-3-(4-methoxy-3-dimethylaminophenyl)propionate(1.56 g) in benzyl alcohol (3.7 ml)and benzene (7.4 ml) was added p-toluenesulfonic acid (0.82 g)and heated under reflux for 6 hours. After cooling, the solvent wasevaporated in vacuo, and the gained crude product was purified bysilica gel column chromatography. The residue was eluted withmixed solvent of hexane, ethyl acetate, and ethanol (60:35:5, v/v).The fractions containing the desired product were combined andevaporated in vacuo to obtain benzyl (R)-2-hydroxy-3-(4-methoxy-3-dimethylaminophenyl)propionate(0.93 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. customwas purified bysilica gel column chromatography
  5. washThe residue was eluted
  6. additioncontaining the desired product

Sources & evidence

ORD record
ord-fc1b289a09284c68a9aaf47cf31477f1
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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