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Hydrochloric Acid → (S)-3-[2-tert-Butoxycarbonyl-2-(3-carboxy-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1809486
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인쇄 미리보기

반응식

HRID 1809486 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@@H:18]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27]C)=[O:26])[C:20]2=[O:29])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@@H:18]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([OH:27])=[O:26])[C:20]2=[O:29])=[CH:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58674958(S)-3-[2-tert-Butoxycarbonyl-2-(3-methoxycarbonyl-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 58674953(S)-3-[2-tert-Butoxycarbonyl-2-(3-carboxy-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 312751,4-Dioxane용매

실험 절차

To a solution of (S)-3-[2-tert-Butoxycarbonyl-2-(3-methoxycarbonyl-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (2.3 g, 4.7 mmol) in dioxane (60 ml) was added a lithium hydroxide (115 mg, 4.7 mmol) in water (30 ml). The mixture was stirred overnight at room temperature. The mixture was diluted with water, acidified to pH-3 with 1M HCl and extracted with ethylacetate. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to afford the crude product as a white solid was used in the next stage without further purification (1.9 g, 85%); 1H NMR (400 MHz, CDCl3) δ 1.45 (9H, s), 1.74 (9H, s), 3.50 (2H, m), 5.65 (1H, br s), 6.08 (1H, t), 7.2-7.5 (5H, m), 8.15 (2H, m);

후처리

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-56493c6210474e7aa45740c581bccf20
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362043B2

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