ethyl N-cyanopropionimidate → HCID 178457586, compound

HRID 2371681Notes

Reaction equation

HRID 2371681 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH2:5][CH3:6])#[N:2].[C:10]([C:12]1[CH:25]=[CH:24][C:15]2[O:16][C:17]([CH3:23])([CH3:22])[C@@H:18]([OH:21])[C@H:19]([NH2:20])[C:14]=2[CH:13]=1)#[N:11]>C(OCC)(=O)C>[C:10]([C:12]1[CH:25]=[CH:24][C:15]2[O:16][C:17]([CH3:23])([CH3:22])[C@@H:18]([OH:21])[C@H:19]([NH:20][C:4](=[N:3][C:1]#[N:2])[CH2:5][CH3:6])[C:14]=2[CH:13]=1)#[N:11]

Participants

4

Reactant 2

HCID 10820532ethyl N-cyanopropionimidateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 178457586HCID 178457586, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.39 g of ethyl N-cyanopropionimidate, 2.17 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-amino-2H-benzo[b]pyran-3-ol was added, and the mixture was reacted under stirring at a temperature of from 100° to 120° C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate Then, ethyl acetate was distilled off under reduced pressure The residual oily substance was purified by silica gel column chromatography to obtain 1.48 g of the above identified compound in the form of crystals.

Workup

  1. customthe mixture was reacted
  2. temperatureThe reaction mixture was cooled
  3. washwashed twice with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationethyl acetate was distilled off under reduced pressure The residual oily substance
  6. customwas purified by silica gel column chromatography
  7. customto obtain 1.48 g of the

Sources & evidence

ORD record
ord-2a12844b5f2b41e3b8d30b759a484cea
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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