Water → N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester

HRID 1464221ノート

反応式

HRID 1464221 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:17](=[O:18])[O:16][C:14](=[O:15])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(O)(O)(=O)=O.[CH3:24][O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH2:28].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH3:24][O:25][C:26](=[O:36])[C@H:27]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:28][C:17](=[O:18])[C@H:12]([CH2:13][C:14](=[O:15])[OH:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

参加物

6

反応物 4

HCID 962WaterHCID 517045Sodium AcetateHCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamateHCID 20841682L-phenylalanine methyl ester sulfate

生成物 1

HCID 10159630N-(Benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester収率 73.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

In 100.4 g of acetic acid, 25.1 g (0.1 mole) of N-benzyloxycarbonyl-L-aspartic anhydride was suspended and 22.7 g (0.1 mole) of L-phenylalanine methyl ester sulfate was added with stirring at 5°-10° C. Successively 17.6 g (0.21 mole) of sodium acetate was added at the same temperature. The reaction was carried out for 4 hours with stirring at the same temperature. Thereafter 87.1 g of water was added to the reaction mixture to adjust the concentration of organic carboxylic acid to 53.5% by weight. After cooling to 0°-5° C., precipitated crystals were filtered, washed and dried. Crystals of N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester were obtained. The yield was 31.2 g (73.1% yield on L-phenylalanine methyl ester sulfate).

後処理

  1. stirringwith stirring at the same temperature
  2. temperatureAfter cooling to 0°-5° C.
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed
  6. customdried

出典と根拠

ORDレコード
ord-a893da5500e64c718ebcd50755c54d72
出典データセット
uspto-grants-1994_04
特許番号
US05302743

反応ノート

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