Diphenylphosphine → N-Acetyl-L-phenylalanine

HRID 1604049Notes

Reaction equation

HRID 1604049 reaction equation
C1(PC2C=CC=CC=2)C=CC=CC=1.[C:14]([NH:17][C:18](=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19]([OH:21])=[O:20])(=[O:16])[CH3:15].[H][H]>C1COCC1>[C:14]([NH:17][C@H:18]([C:19]([OH:21])=[O:20])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 70017DiphenylphosphineHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 74839N-Acetyl-L-phenylalanineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

110 μmol of the optically active diphenylphosphine ligand of Example 3 were dissolved in 5 ml of THF and, after addition of 100 μmol of Rh(COD)2BF4, stirred at RT for 20 min. 100 mmol of α-acetamidocinnamic acid and 250 ml of THF were added to the clear yellow solution. This solution was hydrogenated under 20 bar of hydrogen at 30° C. The reaction was complete after 20 min. N-Acetyl-(S)-phenylalanine was isolated after workup in 97% yield and an optical purity of 99.6% ee.

Workup

  1. waitThe reaction was complete after 20 min

Sources & evidence

ORD record
ord-3f2a37a0976645b0bd905540cdc8ddf3
Source dataset
uspto-grants-1999_11
Patent number
US05990320

Reaction notes

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