Hydrochloric Acid → ethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

HRID 2230401ノート

反応式

HRID 2230401 の反応式
[OH:1][C@@H:2]([C@H:17]([OH:32])[C@H:18]([OH:31])[C@@H:19]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25])[CH2:20][OH:21])[C:3]([NH:5][C@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9])=[O:4].Cl.[CH2:34](O)[CH3:35]>>[OH:1][C@@H:2]([C@H:17]([OH:32])[C@H:18]([OH:31])[C@@H:19]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:28])[CH3:29])[NH2:25])[CH2:20][OH:21])[C:3]([NH:5][C@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([O:10][CH2:34][CH3:35])=[O:9])=[O:4]

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10456696(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid2 回

生成物 1

HCID 59902671ethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

実験手順

To (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid (Compound 3) (500 mg) was added a 28% solution of hydrogen chloride in ethanol (200 ml) and the mixture was stirred at room temperature for 20 hours. After concentration, the residue was subjected to silica gel column chromatography and eluted with acetonitrile-water (5:1). The effective fractions were combined and concentrated under reduced pressure. The residue was dissolved in water (10 ml) and neutralized with aqueous sodium hydrogencarbonate solution. The solution was passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from chloroform-diethylether to afford the title compound (123 mg).

後処理

  1. concentrationAfter concentration
  2. washeluted with acetonitrile-water (5:1)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (10 ml)
  5. washfollowed by elution with water-acetonitrile
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from chloroform-diethylether

出典と根拠

ORDレコード
ord-5626da6ca69a4d3290a5bb85cf81cd60
出典データセット
uspto-grants-2002_07
特許番号
US06423869B1

反応ノート

読み込み中…