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

HRID 1624170

反応式

HRID 1624170 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-9dc477f33f7647648c8cb66158130826
出典データセット
uspto-grants-2014_07
特許番号
US08778991B2

関連ノート

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