Lithium Hydroxide → HCID 86702355、化合物

HRID 1477156ノート

反応式

HRID 1477156 の反応式
C([O:8][C:9](=[O:28])[C@@H:10]([NH:14][C:15](=[O:27])[C@@H:16]([N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[CH3:17])[CH:11]([CH3:13])[CH3:12])C1C=CC=CC=1.[OH-].[Li+]>C1COCC1.CO.O>[C:23]([O:22][C:20]([N:18]([CH3:19])[C@@H:16]([CH3:17])[C:15]([NH:14][C@@H:10]([CH:11]([CH3:12])[CH3:13])[C:9]([OH:28])=[O:8])=[O:27])=[O:21])([CH3:26])([CH3:25])[CH3:24]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 117871378(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid benzyl ester

生成物 1

HCID 86702355HCID 86702355、化合物収率 104.7%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid benzyl ester (7 g, 18 mmol) and 1 M aqueous lithium hydroxide (40 mL, 40 mmol) was added to THF/MeOH/H2O (3:1:1; 200 mL) to give a yellow solution. The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in water and then acidified to pH 2 using first 6 M and then 1 M aqueous HCl. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give crude (S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyric acid (5.7 g) which was used directly in the next step without further purification, m/z=303 (M+H).

後処理

  1. customto give a yellow solution
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f12e7ce2984b49c1b806593c30d0e19f
出典データセット
uspto-grants-2016_08
特許番号
US09403768B2

反応ノート

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