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 1477158노트

반응식

HRID 1477158 반응식
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]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 117872741HCID 117872741, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

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온도
23 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-972d262fd7804f75a0d015842f5aef75
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403768B2

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