ethyl N-carbonylcarbamate → 3-Amino-2-ethoxycarbonylaminocarbonyl-but-2-enoic acid methyl ester

HRID 1091945Notes

Reaction equation

HRID 1091945 reaction equation
[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[CH2:9]([O:11][C:12]([N:14]=[C:15]=[O:16])=[O:13])[CH3:10]>C(OCC)C>[CH3:7][O:6][C:4](=[O:5])[C:3]([C:15]([NH:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])=[O:16])=[C:2]([NH2:1])[CH3:8]

Participants

4

Reactant 2

HCID 300166ethyl N-carbonylcarbamateHCID 643918Methyl 3-aminocrotonate

Product 1

HCID 765579213-Amino-2-ethoxycarbonylaminocarbonyl-but-2-enoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of methyl 3-aminocrotonate (39.0 g, 0.339 mol) in anhydrous diethyl ether (200 mL) under nitrogen with magnetic stirring at 0-5° C. is added in dropwise fashion a solution of ethoxycarbonyl isocyanate (0.339 mol) in diethyl ether (40 mL). The resulting pale yellow colored suspension is stirred below 5° C. for 4 h. The solid is collected by suction filtration, rinsed with 50 mL of diethyl ether and dried under vacuum at room temperature for 30 h to obtain the title compound as an off-white solid.

Workup

  1. filtrationThe solid is collected by suction filtration
  2. washrinsed with 50 mL of diethyl ether
  3. customdried under vacuum at room temperature for 30 h

Sources & evidence

ORD record
ord-cb22977511bf4a38aae56364a7cb180e
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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