Ethyl allyl(2-oxoethyl)carbamate → HCID 10883617, compound

HRID 1857989Notes

Reaction equation

HRID 1857989 reaction equation
[CH2:1]([N:4]([CH2:10][CH:11]=O)[C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH:2]=[CH2:3].[CH2:13]([NH:20][CH:21]([CH2:25][CH2:26][CH:27]1[O:32][CH2:31][CH2:30][CH2:29][O:28]1)C(O)=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH2:13]([N:20]1[CH:21]([CH2:25][CH2:26][CH:27]2[O:28][CH2:29][CH2:30][CH2:31][O:32]2)[CH2:3][CH:2]2[CH:11]1[CH2:10][N:4]([C:5]([O:6][CH2:7][CH3:8])=[O:9])[CH2:1]2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11084330Ethyl allyl(2-oxoethyl)carbamateHCID 22125682HCID 22125682, compound

Product 1

HCID 10883617HCID 10883617, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-allyl-N-(2-oxoethyl)carbamic acid, ethyl ester (Schenke, T.; Peterson, U. Eur. patent EPO393424A2, 1992) (0.203 g, 1.19 mmol) and 2-benzylamino-4-(1,3-dioxan-2-yl)butyric acid (0.330 g, 1.18 mmol) in anhydrous toluene (5 mL) was heated at reflux under argon for 24 h. After cooling, the solvents were removed in vacuo and the residue was purified by flash chromatography (silica gel, 50% EtOAc/petroleum ether) to give 0.3234 g (71%) of the title compound as a yellow oil. δH (360 MHz, CDCl3) 1.26 (3H, m), 1.28-1.40 (2H, m), 1.48-1.89 (5H, m), 2.05 (1H, m), 2.69 (1H, m), 2.94 (1H, m), 3.10 (1H, m), 3.30-3.47 (4H, m), 3.58 (1H, m), 3.74 (2H, td), 3.92 (1H, d, J=13.6 Hz), 4.07-4.14 (4H, m), 4.48 (1H, t, J=5.0 Hz), 7.22-7.34 (5H, m). m/e (ES+) 389 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 24 h
  3. temperatureAfter cooling
  4. customthe solvents were removed in vacuo
  5. customthe residue was purified by flash chromatography (silica gel, 50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-a49bd1d024c9456da8b881530044c6c1
Source dataset
uspto-grants-2000_11
Patent number
US06150391

Reaction notes

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