Ethanol → 7-[(1R)-2-Amino-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one, acetate salt

HRID 470948ノート

反応式

HRID 470948 の反応式
[N:1]([CH2:4][C@@H:5]([C:7]1[C:15]2[S:14][C:13](=[O:16])[NH:12][C:11]=2[C:10]([OH:17])=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-].C([OH:20])C>[Pd]>[C:10]([OH:17])(=[O:20])[CH3:11].[NH2:1][CH2:4][C@@H:5]([C:7]1[C:15]2[S:14][C:13](=[O:16])[NH:12][C:11]=2[C:10]([OH:17])=[CH:9][CH:8]=1)[OH:6]

参加物

4

反応物 2

HCID 702EthanolHCID 866367487-[(1R)-2-Azido-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one

生成物 1

HCID 671669747-[(1R)-2-Amino-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one, acetate salt

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

5% Palladium on carbon type 87L paste (22 g) was added to 7-[(1R)-2-azido-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one (example 1, step c) (225 g) dissolved in ethanol (3 L). The reaction was stirred under hydrogen (3 bar) for 48 h. A further 10 g of the catalyst was added and hydrogenation continued for a further 5 days. The reaction mixture was filtered and the solid (product+catalyst) suspended in ethanol (2.5 L) then acetic acid (150 mL) was added and the whole stirred overnight. The mixture was filtered again to remove the palladium on carbon catalyst. The solution was evaporated to dryness and azeotroped with toluene (2×1 L). The solid was slurried in tetrahydrofuran (1 L) for 4 hours, filtered and dried at 40° C. in vacuo to give the subtitled compound. Yield 57 g.

後処理

  1. waithydrogenation continued for a further 5 days
  2. filtrationThe reaction mixture was filtered
  3. additionacetic acid (150 mL) was added
  4. stirringthe whole stirred overnight
  5. filtrationThe mixture was filtered again
  6. customto remove the palladium on carbon catalyst
  7. customThe solution was evaporated to dryness
  8. customazeotroped with toluene (2×1 L)
  9. waitThe solid was slurried in tetrahydrofuran (1 L) for 4 hours
  10. filtrationfiltered
  11. customdried at 40° C. in vacuo

出典と根拠

ORDレコード
ord-2f8972e38d444b8b81d47d5e1e83dd9f
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

読み込み中…