Triethylamine → Tert-butyl 3-(2-ethoxy-2-oxoethyl)-3-(5-(phenylethynyl)furan-2-carboxamido)-azetidine-1-carboxylate

HRID 1192913ノート

反応式

HRID 1192913 の反応式
[NH2:1][C:2]1([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.CCN(CC)CC.[C:26]1([C:32]#[C:33][C:34]2[O:38][C:37]([C:39](ON3C(=O)CCC3=O)=[O:40])=[CH:36][CH:35]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C:2]1([NH:1][C:39]([C:37]2[O:38][C:34]([C:33]#[C:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:35][CH:36]=2)=[O:40])[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])[CH2:3]1)[CH3:18]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 574408102,5-Dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylateHCID 58109966Tert-butyl 3-amino-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

生成物 1

HCID 66865345Tert-butyl 3-(2-ethoxy-2-oxoethyl)-3-(5-(phenylethynyl)furan-2-carboxamido)-azetidine-1-carboxylate収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of tert-butyl 3-amino-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate (130 mg, 0.503 mmol) in DMF (3 mL) was treated with NEt3 (0.19 mL, 1.37 mmol), and 2,5-dioxopyrrolidin-1-yl 5-(phenylethynyl)furan-2-carboxylate, prepared as described in Preparation 5 (141 mg, 0.457 mmol). The reaction was stirred overnight, at room temperature, then the solvent removed in vacuo and the crude product purified by column chromatography to obtain the title compound (168 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 7.57 (m, 2H), 7.40 (m, 3H), 7.12 (s, 1H), 7.04 (s, 1H), 6.70 (s, 1H), 4.17 (m, 4H), 4.03 (d, 2H, J=9.6 Hz), 3.17 (s, 2H), 1.45 (s, 9H), 1.26 (t, 3H, J=7.2 Hz); MS ESI 453.2 [M+H]+, calcd for [C25H28N2O6+H]+ 453.51.

後処理

  1. customprepared
  2. customthe solvent removed in vacuo
  3. customthe crude product purified by column chromatography

出典と根拠

ORDレコード
ord-5e23ef891c124963aa390eb1d192fc06
出典データセット
uspto-grants-2014_03
特許番号
US08680282B2

反応ノート

読み込み中…