Dicyclohexylcarbodiimide → 1-(N-Methoxyacetylglycyl)-2-cyanoaziridine

HRID 2286568

Reaction equation

HRID 2286568 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][CH2:7][C:8]([OH:10])=O)=[O:5].[C:11]([CH:13]1[CH2:15][NH:14]1)#[N:12].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:1][O:2][CH2:3][C:4]([NH:6][CH2:7][C:8]([N:14]1[CH2:15][CH:13]1[C:11]#[N:12])=[O:10])=[O:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 118115Aziridine-2-carbonitrileHCID 16775934N-(Methoxyacetyl)glycine

Product 1

HCID 234615891-(N-Methoxyacetylglycyl)-2-cyanoaziridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.94 g. N-Methoxyacetylglycine are dissolved in 29 ml. tetrahydrofuran and mixed, with stirring and ice cooling, with 1.36 g. 2-cyanoaziridine and 4.3 g. dicyclohexylcarbodiimide, whereafter the reaction mixture is stirred for 2 hours. After filtering off the dicyclohexylurea, from the filtrate there are obtained 2.8 g. of crystals which, for purification, are dissolved in ethyl acetate and reprecipitated with ligroin. There is thus obtained 1-(N-methoxyacetylglycyl)-2-cyanoaziridine; M.p. 70°-72° C.

Workup

  1. filtrationAfter filtering off the dicyclohexylurea
  2. customfrom the filtrate there are obtained 2.8 g
  3. customof crystals which, for purification
  4. dissolutionare dissolved in ethyl acetate
  5. customreprecipitated with ligroin

Sources & evidence

ORD record
ord-67e7568198d34822ac72e76ba96baac0
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Linked notes

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