3-Ethoxythiophene-2-carboxylic acid → (S)-methyl 2-(3-ethoxy-N-methylthiophene-2-carboxamido)pent-4-enoate

HRID 501677ノート

反応式

HRID 501677 の反応式
[CH3:1][NH:2][C@@H:3]([CH2:8][CH:9]=[CH2:10])[C:4]([O:6][CH3:7])=[O:5].[CH2:11]([O:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([OH:21])=O)[CH3:12]>>[CH2:11]([O:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([N:2]([C@@H:3]([CH2:8][CH:9]=[CH2:10])[C:4]([O:6][CH3:7])=[O:5])[CH3:1])=[O:21])[CH3:12]

参加物

3

反応物 2

HCID 27776523-Ethoxythiophene-2-carboxylic acidHCID 14732247(S)-Methyl 2-(methylamino)pent-4-enoate

生成物 1

HCID 68466211(S)-methyl 2-(3-ethoxy-N-methylthiophene-2-carboxamido)pent-4-enoate

実験手順

Step N (1): (S)-Methyl 2-(methylamino)pent-4-enoate from Step G (1) and 3-ethoxythiophene-2-carboxylic acid were coupled according to the procedure outlined in Step A (1). The product was purified using silica gel column chromatography to provide 80 mg (quantitative yield) of (S)-methyl 2-(3-ethoxy-N-methylthiophene-2-carboxamido)pent-4-enoate. LC-MS (M+H)+=298.29; 1H NMR (300 MHz, CDCl3) δ ppm 1.32 (t, J=6.77 Hz, 3H) 2.48-2.64 (m, 1H) 2.68-2.82 (m, 1H) 3.01 (s, 3H) 3.72 (s, 3H) 4.06 (q, J=6.83 Hz, 2H) 5.00-5.20 (m, 3H) 5.63-5.84 (m, 1H) 6.70 (d, J=5.49 Hz, 1H) 7.29 (d, J=5.49 Hz, 1H).

後処理

  1. customThe product was purified

出典と根拠

ORDレコード
ord-32df5fa51fd740579afcf28a6d3dedc9
出典データセット
uspto-grants-2010_08
特許番号
US07772221B2

反応ノート

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