2-(3-Methoxy-allylidene)-malonic acid dimethyl ester → (S)-3-[2-tert-Butoxycarbonyl-2-(3-methoxycarbonyl-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1809485

반응식

HRID 1809485 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]([NH2:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][C:29](=[O:40])[C:30](=[CH:35][CH:36]=[CH:37]OC)[C:31](OC)=[O:32].C[O-].[Na+]>CO.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:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:26]2[CH:37]=[CH:36][CH:35]=[C:30]([C:29]([O:28][CH3:27])=[O:40])[C:31]2=[O:32])=[CH:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

참가 물질

6

반응물 3

HCID 5979922-(3-Methoxy-allylidene)-malonic acid dimethyl esterHCID 7021141tert-butyl 3-[(2S)-2-amino-3-(tert-butoxy)-3-oxopropyl]-1H-indole-1-carboxylateHCID 10942334Sodium Methoxide

생성물 1

HCID 58674958(S)-3-[2-tert-Butoxycarbonyl-2-(3-methoxycarbonyl-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester수율 66.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of (S)-3-(2-Amino-2-tert-butoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester (2.5 g, 7 mmol) in methanol (15 ml) was added 2-(3-methoxy-allylidene)-malonic acid dimethyl ester (1.5 g, 7 mmol) and stirred overnight at room temperature. Sodium methoxide (78 mg, 1.4 mmol) was added and stirred for three hours at room temperature. The reaction mixture was diluted with water (50 ml) and extracted with ethylacetate (60 ml). The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to afford the crude product, which was perified by flash chromatography (30-70% ethylacetate/petroleum ether) to afford the title compound as a white solid (2.3 g, 57%); 1H NMR (400 MHz, CDCl3) δ 1.43 (9H, s), 1.72 (9H, s), 3.50 (2H, m), 3.91 (3H, m), 5.68 (1H, br s), 6.08 (1H, t), 7.2-7.5 (5H, m), 8.15 (2H, m); M+H 497.5, M−H 495.5.

후처리

  1. stirringstirred for three hours at room temperature
  2. extractionextracted with ethylacetate (60 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford the crude product, which

출처 및 근거

ORD 기록
ord-38fcff9909d849b1905c205bec0fe92c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362043B2

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