(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile → HCID 178431172, compound

HRID 2371684Notes

Reaction equation

HRID 2371684 reaction equation
[C:1]([N:3]=[C:4](OCC)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)#[N:2].[C:14]([C:16]1[CH:29]=[CH:28][C:19]2[O:20][C:21]([CH3:27])([CH3:26])[C@@H:22]([OH:25])[C@H:23]([NH2:24])[C:18]=2[CH:17]=1)#[N:15]>CN(C)C=O.C(OCC)(=O)C>[C:14]([C:16]1[CH:29]=[CH:28][C:19]2[O:20][C:21]([CH3:27])([CH3:26])[C@@H:22]([OH:25])[C@H:23]([NH:24][C:4](=[N:3][C:1]#[N:2])[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:18]=2[CH:17]=1)#[N:15]

Participants

5

Reactant 2

HCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrileHCID 12666260HCID 12666260, compound

Product 1

HCID 178431172HCID 178431172, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.89 g of ethyl N-cyanobenzimidate was dissolved in 5 ml of dimethylformamide, and 2.15 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-amino-2H-benzo[b]pyran-3-ol was added thereto. The mixture was reacted 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 four times 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 1.32 g of the above identified compound in the form of crystals.

Workup

  1. customThe mixture was reacted at a temperature of from 100° to 120° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed four times with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, ethyl acetate was distilled off under reduced pressure
  6. customThe residual oily substance was purified by silica gel column chromatography
  7. customto obtain 1.32 g of the

Sources & evidence

ORD record
ord-986d5650d1fa4ebab8dbe4c6cab4ea1a
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

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