Lithium Hydroxide → (S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-indole-2-carboxylic acid

HRID 1477158ノート

反応式

HRID 1477158 の反応式
C([O:3][C:4]([C@@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]1[C:15](=[O:34])[C@@H:16]([NH:20][C:21](=[O:33])[C@@H:22]([N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25])[CH3:23])[CH:17]([CH3:19])[CH3:18])=[O:5])C.[OH-].[Li+]>C1COCC1.O.CO>[C:29]([O:28][C:26]([N:24]([CH3:25])[C@@H:22]([CH3:23])[C:21]([NH:20][C@@H:16]([CH:17]([CH3:18])[CH3:19])[C:15]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][C@H:6]1[C:4]([OH:5])=[O:3])=[O:34])=[O:33])=[O:27])([CH3:32])([CH3:31])[CH3:30]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 117872741HCID 117872741、化合物

生成物 1

HCID 118340313(S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-indole-2-carboxylic acid収率 97.9%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
23 °C

実験手順

To a solution of (S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester (2.93 g, 6.16 mmol) in THF/water/methanol (3:1:1; 60 mL) was added 1 M aqueous lithium hydroxide (18.5 mL, 18.5 mmol). The reaction mixture was stirred at 23° C. for 2.5 h and then concentrated in vacuo. The residue was diluted with water and acidified with 6 M and then 1 M aqueous HCl to pH˜2. The mixture was extracted with EtOAc, the organic layer was dried over Na2SO4 and concentrated in vacuo to give (S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-indole-2-carboxylic acid (2.70 g) as an off-white foam, m/z=470 (M+Na).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-972d262fd7804f75a0d015842f5aef75
出典データセット
uspto-grants-2016_08
特許番号
US09403768B2

反応ノート

読み込み中…