Benzene → N-acetyl-(R)-phenyl-alanine

HRID 223789

反応式

HRID 223789 の反応式
[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]

参加物

6

反応物 3

HCID 241BenzeneHCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 178418361HCID 178418361、化合物

生成物 1

HCID 821174N-acetyl-(R)-phenyl-alanine収率 99%

試薬・触媒・溶媒 2

HCID 86738616cyclo-octadiene-((S)-1,2-Bis-(diphenylphosphino)-3-phenyl-propane)-rhodium-tetrafluoroborate触媒HCID 702Ethanol溶媒2 回

実験手順

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%.

出典と根拠

ORDレコード
ord-008c63fd9da74710bae5d9f2cc8ef5fc
出典データセット
uspto-grants-1982_10
特許番号
US04356324

関連ノート

読み込み中…