N-Tosyl-D-phenylalanine → N-((4-Methylphenyl)sulfonyl)-L-phenylalanine

HRID 1436901Notes

Reaction equation

HRID 1436901 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([C:19]([OH:21])=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1>C(OCC)(=O)C.C(OCC)C>[C:1]1([CH3:22])[CH:2]=[CH:3][C:4]([S:7]([NH:10][C@H:11]([C:19]([OH:21])=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 686492N-Tosyl-D-phenylalanine

Product 1

HCID 99327N-((4-Methylphenyl)sulfonyl)-L-phenylalanineYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 50 ml of ethyl acetate and 50 ml of diethylether were dissolved under heating 7.4 g of 2,4-cis-4-ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)piperidine and 4.0 g of N-p-toluenesulfonyl-D-phenylalanine. The solvent was concentrated by heating, 30 ml of diisopropyl ether was added thereto and the mixture was stirred. Precipitated crystals were removed and mother liquor was washed with a concentrated aqueous ammonia solution, dried and concentrated under reduced pressure. To the residue was added 4.0 g of N-p-toluenesulfonyl-L-phenylalanine, and 50 ml of ethyl acetate and 30 ml of diisopropyl ether were added thereto and dissolved by heating, the mixture was stirred at room temperature for 16 hours. Precipitated crystals were collected by filtration, washed with diisopropyl ether, and dried, to give 4.0 g of N-p-toluenesulfonyl-L-phenylalanine salt of (2R,4S)-4-ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)-4-piperidine.

Workup

  1. dissolutionwere dissolved
  2. concentrationThe solvent was concentrated
  3. temperatureby heating
  4. addition30 ml of diisopropyl ether was added
  5. customPrecipitated crystals
  6. customwere removed
  7. washmother liquor was washed with a concentrated aqueous ammonia solution
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. additionTo the residue was added 4.0 g of N-p-toluenesulfonyl-L-phenylalanine, and 50 ml of ethyl acetate and 30 ml of diisopropyl ether
  11. additionwere added
  12. dissolutiondissolved
  13. temperatureby heating
  14. stirringthe mixture was stirred at room temperature for 16 hours
  15. customPrecipitated crystals
  16. filtrationwere collected by filtration
  17. washwashed with diisopropyl ether
  18. customdried

Sources & evidence

ORD record
ord-649909d0bb9e4ef482ec0e0b1ff8ebbb
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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