Cesium bicarbonate → 4-{2-[(2E)-3-(Methoxycarbonyl)prop-2-enoyloxy]acetylamino}butanoic acid

HRID 1624169

반응식

HRID 1624169 반응식
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].Cl[CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[O:13].C(=O)([O-])O.[Cs+]>CN1C(=O)CCC1>[CH3:9][O:8][C:1](/[CH:2]=[CH:3]/[C:4]([O:6][CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:13])=[O:5])=[O:7]

참가 물질

5

반응물 3

HCID 2734983Cesium bicarbonateHCID 5369209Monomethyl FumarateHCID 86667136Tert-butyl 4-(2-chloroacetylamino)butanoate

생성물 1

HCID 461791554-{2-[(2E)-3-(Methoxycarbonyl)prop-2-enoyloxy]acetylamino}butanoic acid수율 46%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Following general procedure A, methyl hydrogen fumarate (MHF) (0.56 g, 4.33 mmol) dissolved in NMP was reacted at ca. 55° C. with tert-butyl 4-(2-chloroacetylamino)butanoate (0.85 g, 3.61 mmol) in the presence of CsHCO3 (0.98 g, 5.05 mmol) of the tert-butyl-protected intermediate and then purified by silica gel column chromatography (Biotage) using a mixture of ethyl acetate (EtOAc) and hexanes (1:1) as eluent. The purified product was treated with 50% trifluoroacetic acid (TFA) in dichloromethane (DCM). Removal of solvents afforded 0.45 g (46% yield) of the title compound (7). 1H NMR (CD3OD, 400 MHz): δ 6.94-6.91 (m, 2H), 4.65 (s, 2H), 3.81 (s, 3H), 3.28 (t, J=6.8 Hz, 2H), 2.33 (t, J=7.2 Hz, 2H), 1.81 (p, J=7.1 Hz, 2H). MS (ESI): m/z 274.03 (M+H)+272.06 (M−H)−.

후처리

  1. custompurified by silica gel column chromatography (Biotage)
  2. additiona mixture of ethyl acetate (EtOAc) and hexanes (1:1) as eluent
  3. additionThe purified product was treated with 50% trifluoroacetic acid (TFA) in dichloromethane (DCM)
  4. customRemoval of solvents

출처 및 근거

ORD 기록
ord-91115aa74c93497c904fe32806dd676b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778991B2

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