Benzene → N-acetyl-(R)-phenyl-alanine

HRID 223789

Reaction equation

HRID 223789 reaction equation
[C:1]([NH:4][C:5](=[CH:9]C1C=CC=CC=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>F[B-](F)(F)F.[Rh+3].C1(P(C2C=CC=CC=2)C[C@@H](P(C2C=CC=CC=2)C2C=CC=CC=2)CC2C=CC=CC=2)C=CC=CC=1.C1CCCCC=CC=1.F[B-](F)(F)F.F[B-](F)(F)F.CCO>[C:1]([N:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:5]([C:6]([OH:8])=[O:7])[CH3:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 241BenzeneHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 821174N-acetyl-(R)-phenyl-alanineYield 99%

Reagents, catalysts & solvents 2

HCID 86738616cyclo-octadiene-((S)-1,2-Bis-(diphenylphosphino)-3-phenyl-propane)-rhodium-tetrafluoroborateCatalystHCID 702EthanolSolvent2×

Procedure

There were added saturated solution of α-acetamido cinnamic acid in a mixture of 2 parts by volume of ethanol and 1 part by volume of benzene 7.9 mg of the catalyst produced in Example 12. The reaction mixture was sucked into an evacuated 100 ml autoclave and pressurized with 17 bars of hydrogen pressure. After working up in the manner as described in Example 6, there were isolated 4.4 grams of N-acetyl-(R)-phenyl-alanine having a rotary value of [α]D20 =-46.5° (c=1/95% EtOH), corresponding to an optical yield of 99%.

Sources & evidence

ORD record
ord-008c63fd9da74710bae5d9f2cc8ef5fc
Source dataset
uspto-grants-1982_10
Patent number
US04356324

Linked notes

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