D-Phenylalanine → HCID 86750269, compound

HRID 1600427Notes

Reaction equation

HRID 1600427 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(O)C>[C:14]1([CH3:24])[CH:15]=[CH:16][C:17]([S:20]([OH:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1.[CH2:14]([O:11][C:10](=[O:12])[C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1])[CH3:15]

Participants

4

Reactant 2

HCID 71567D-PhenylalanineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86750269HCID 86750269, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of D-phenylalanine (5.0 g, 30 mmol) and p-toluenesulfonic acid monohydrate (12.7 g, 67 mmol) in 150 mL of anhydrous ethanol was refluxed for 24 hours. After cooling to room temperature, the solvent was removed by rotary evaporator, the residue triturated with diethyl ether, filtered and dried in vacuo over P2O5 to give the p-toluenesulfonate salt of the title compound (9.7 g) as a white solid and the structure verified by NMR.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe solvent was removed by rotary evaporator
  3. customthe residue triturated with diethyl ether
  4. filtrationfiltered
  5. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-1487c7dfaa7a40ddb11562f4967b80f5
Source dataset
uspto-grants-1998_04
Patent number
US05744631

Reaction notes

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