Ammonia → HCID 19848787, compound

HRID 1905130Notes

Reaction equation

HRID 1905130 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-2e8db0d55c954c60ac10c76c0fa64549
Source dataset
uspto-grants-1989_06
Patent number
US04841078

Reaction notes

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