Benzene → N-acetyl-(R)-phenyl-alanine

HRID 223789

반응식

HRID 223789 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 86738616cyclo-octadiene-((S)-1,2-Bis-(diphenylphosphino)-3-phenyl-propane)-rhodium-tetrafluoroborate촉매HCID 702Ethanol용매2회

실험 절차

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%.

출처 및 근거

ORD 기록
ord-008c63fd9da74710bae5d9f2cc8ef5fc
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04356324

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