Ammonia → HCID 19848787, compound

HRID 2118916Notes

Reaction equation

HRID 2118916 reaction equation
C([O:4][C:5]1[C:10]2[CH2:11][CH:12]([CH2:17][CH2:18][C:19]([O-])=[O:20])[C:13]([CH3:16])([CH3:15])[O:14][C:9]=2[CH:8]=[C:7]([O:22][CH:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:24])[CH:6]=1)(=O)C.[NH3:34]>CO>[OH:4][C:5]1[C:10]2[CH2:11][CH:12]([CH2:17][CH2:18][C:19]([NH2:34])=[O:20])[C:13]([CH3:16])([CH3:15])[O:14][C:9]=2[CH:8]=[C:7]([O:22][CH:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:24])[CH:6]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 86739785HCID 86739785, compound

Product 1

HCID 19848787HCID 19848787, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl dl-3-[5-acetoxy-2,2-dimethyl-7-(5-phenyl-2-pentyloxy)-3,4-dihydro-2H-benzopyran-3-yl]propionate, 4.68 g (0.01 mole), is dissolved in methanol and anhydrous ammonia is passed through the mixture at room temperature. The resulting mixture is heated at reflux for two hours while passing ammonia through it. After standing overnight the volatiles are removed by evaporation and the residue purified by column chromatography on silica gel to provide dl-3-[5-hydroxy-2,2-dimethyl-7-(5-phenyl-2-pentyloxy)-3,4-dihydro-2H-benzopyran-3-yl]propionamide.

Workup

  1. customis passed through the mixture at room temperature
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for two hours
  4. customthe volatiles are removed by evaporation
  5. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-46e6d94201e14f8d80a716006038dbde
Source dataset
uspto-grants-1987_07
Patent number
US04680404

Reaction notes

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