L-Phenylalanine → Cyclohexyl acetate

HRID 429591

反応式

HRID 429591 の反応式
[CH:1]1(N[C@H](C(O)=O)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N[C@H:14]([C:22]([OH:24])=[O:23])CC1C=CC=CC=1.C1(NCC(O)=O)CCCCC1.C1C=CC([C@@H](N)C(O)=O)=CC=1>[Pt]=O.[OH-].[Pd+2].[OH-].C(O)(=O)C>[C:22]([O:24][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)(=[O:23])[CH3:14]

参加物

8

反応物 4

HCID 6140L-PhenylalanineHCID 42810Glycine, N-cyclohexyl-HCID 70134Phenylglycine, D-HCID 12003067(S)-2-(Cyclohexylamino)propanoic acid

生成物 1

HCID 12146Cyclohexyl acetate収率 24%

試薬・触媒・溶媒 3

HCID 82844Platinum oxide (PtO)触媒HCID 9942167Palladium hydroxide触媒HCID 176Acetic Acid溶媒

実験手順

Specific examples of the production of an amino acid which is optically active and contains a cyclohexyl group include the production of cyclohexylalanine by reducing L-phenylalanine in an aqueous acetic acid solution using a platinum oxide catalyst (J. Org. Chem., 1988, 53, 873 and Tetrahedron, 1992, 48, 307), and the production of cyclohexylglycine by reducing (R)-phenylglycine in a carbon-containing aqueous solution using a palladium hydroxide catalyst (Synth. Commun., 1978, 8, 345). However, in the former case, the optical purity of the product is unclear. In the latter case, the yield is as low as between 24 and 66%, and cyclohexyl acetate is formed as a by-product at a ratio of from 27 to 68%. Further, the optical purity of the resulting cyclohexylglycine is between 66 and 84% ee, which is not satisfactory. Accordingly, these methods are not useful on an industrial scale.

後処理

  1. additioncontaining aqueous solution

出典と根拠

ORDレコード
ord-6977f84da42946c585bfff5dd0e69369
出典データセット
uspto-grants-2001_11
特許番号
US06316660B1

関連ノート

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