6-Acetylaminocaproic acid → 1-(6-Acetylaminohexanoyl)-2-cyanoaziridine

HRID 2286569Notes

Reaction equation

HRID 2286569 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)(=[O:3])[CH3:2].[C:13]([CH:15]1[CH2:17][NH:16]1)#[N:14].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([N:16]1[CH2:17][CH:15]1[C:13]#[N:14])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 20056-Acetylaminocaproic acidHCID 10868DicyclohexylcarbodiimideHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 234614311-(6-Acetylaminohexanoyl)-2-cyanoaziridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.46 g. 6-Acetylaminohexanoic acid, 1.36 g. 2-cyanoaziridine and 4.3 g. dicyclohexylcarbodiimide are reacted in the usual manner in 35 ml. tetrahydrofuran and the reaction mixture then worked up to give 1.1 g. 1-(6-acetylaminohexanoyl)-2-cyanoaziridine which, after recrystallization from ethyl acetate-ligroin, melts at 74°-77° C.

Workup

  1. customto give 1.1 g
  2. custom1-(6-acetylaminohexanoyl)-2-cyanoaziridine which, after recrystallization from ethyl acetate-ligroin, melts at 74°-77° C.

Sources & evidence

ORD record
ord-5ed2d50db136443eb96c05537d095a21
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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