Diethyl acetylenedicarboxylate → HCID 67371898, compound

HRID 1753198Notes

Reaction equation

HRID 1753198 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[C:2]#[C:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:32])[CH2:22][NH:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:17][CH:16]=1>C(O)C>[C:28]([O:27][C:25]([NH:24][N:23]([C:2](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:1]([O:10][CH2:11][CH3:12])=[O:9])[CH2:22][C:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=1)=[O:32])=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 67370116HCID 67370116, compound

Product 1

HCID 67371898HCID 67371898, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl but-2-ynedioate (1.6 equivalents) was added to a stirred solution of crude tert-butyl 2-[2-(4-methoxyphenyl)-2-oxoethyl]hydrazinecarboxylate (2 g) in ethanol at 0° C. The reaction was monitored by LCMS. Upon completion, the reaction mixture was concentrated in vacuo to give crude diethyl 2-{2-(tert-butoxycarbonyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]hydrazinyl}but-2-enedioate (1.3 g). The material was carried through without purification. ESI-MI m/z [M+H]+ 451.

Workup

  1. concentrationUpon completion, the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f88f3556793049a4af56f3ec741f6cd0
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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