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

HRID 1192913Notes

Reaction equation

HRID 1192913 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5e23ef891c124963aa390eb1d192fc06
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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