N-Methylol-alpha-chloroacetamide → (N-Methoxy-N-methylcarbamoyl)methyl methyl(2E)but-2-ene-1,4-dioate

HRID 1685614

반응식

HRID 1685614 반응식
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].O[CH2:11][NH:12][C:13](=[O:16])[CH2:14]Cl.[C:17](=O)([O-])[OH:18].[Cs+]>CN1C(=O)CCC1>[C:4]([O:6][CH2:14][C:13](=[O:16])[N:12]([O:18][CH3:17])[CH3:11])(=[O:5])/[CH:3]=[CH:2]/[C:1]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 62466N-Methylol-alpha-chloroacetamideHCID 2734983Cesium bicarbonateHCID 5369209Monomethyl Fumarate

생성물 1

HCID 46179157(N-Methoxy-N-methylcarbamoyl)methyl methyl(2E)but-2-ene-1,4-dioate수율 61%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Following general procedure A, methyl hydrogen fumarate (MHF) (0.50 g, 3.84 mmol) dissolved in NMP was reacted at ca. 55° C. with N-methyl, N-hydroxymethyl chloroacetamide (0.63 g, 4.61 mmol) in the presence of CsHCO3 (0.89 g, 4.61 mmol). The crude material precipitated out from a concentrated ethyl acetate (EtOAc) solution. The solid was filtered off and dried in vacuum to provide 0.54 g (61% yield) of the title compound (10) as a white solid. 1H NMR (CD3OD, 400 MHz): δ 6.92-6.89 (m, 2H), 5.01 (s, 2H), 3.80 (s, 3H), 3.78 (s, 3H), 3.20 (s, 3H). MS (ESI): m/z 232.06 (M+H)+.

후처리

  1. customThe crude material precipitated out from a concentrated ethyl acetate (EtOAc) solution
  2. filtrationThe solid was filtered off
  3. customdried in vacuum

출처 및 근거

ORD 기록
ord-b878a703d00245bc82ef039cda214849
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148414B2

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