2-Methylaziridine → HCID 58319694, compound

HRID 2384310Notes

Reaction equation

HRID 2384310 reaction equation
[CH3:1][C:2](=[CH2:19])[C:3]([O:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15](=[O:18])[CH:16]=[CH2:17])=[O:10])=[O:4].[CH3:20][CH:21]1[CH2:23][NH:22]1>>[CH3:19][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15](=[O:18])[CH2:16][CH2:17][N:22]1[CH2:23][CH:21]1[CH3:20])=[O:10])=[O:4]

Participants

3

Reactant 2

HCID 63772-MethylaziridineHCID 14298189HCID 14298189, compound

Product 1

HCID 58319694HCID 58319694, compoundYield 98.8%

Procedure

The product of Step 1 (2-({[2-(acryloyloxy)ethoxy]carbonyl}amino)ethyl 2-methylacrylate, 10.0 g, 37 mmol) was mixed with 2-methylaziridine (2.8 g, about 44 mmol, 90% pure, available from Aldrich) to cause a slight exotherm. The reaction mixture was allowed to stand at room temperature overnight. Excess 2-methylaziridine was removed at reduced pressure to leave the desired product (12.0 g) as a colorless liquid. NMR and IR spectral analyses confirmed the structure of the product.

Workup

  1. customExcess 2-methylaziridine was removed at reduced pressure

Sources & evidence

ORD record
ord-730c351fb9e24c748dca28d9192f087f
Source dataset
uspto-grants-2012_09
Patent number
US08263711B2

Reaction notes

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