Ammonia → HCID 57000327, compound

HRID 1420763Notes

Reaction equation

HRID 1420763 reaction equation
[O:1]1[C@H:3]2[C:4]3[CH:13]=[C:12]([S:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=4)(=[O:16])=[O:15])[CH:11]=[CH:10][C:5]=3[O:6][C:7]([CH3:9])([CH3:8])[C@@:2]12[CH3:25].[NH3:26]>C(O)C>[NH2:26][C@H:3]1[C@@:2]([OH:1])([CH3:25])[C:7]([CH3:8])([CH3:9])[O:6][C:5]2[CH:10]=[CH:11][C:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)(=[O:16])=[O:15])=[CH:13][C:4]1=2

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 57193476HCID 57193476, compound

Product 1

HCID 57000327HCID 57000327, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

(3S,4S)-3,4-Dihydro-3,4-epoxy-6-(3-methoxyphenyl)sulphonyl-2,2,3-trimethyl-2H-benzo[b]pyran (2.0 g) (see Preparation 17) was dissolved in ethanol (15 ml) and 35% aqueous ammonia solution (10 ml) was added. The mixture was heated at 50° C. for 48 hours before adding further ammonia solution (5 ml) and heating for another 8 hours. The solvent was removed under reduced pressure and the residue was chromatographed on silica using 5:95 methanol:dichloromethane as the eluent to yield (3S,4R)-4-amino-3,4-dihydro-3-hydroxy-6-(3-methoxyphenyl)sulphonyl-2,2,3-trimethyl-2H-benzo[b]pyran (1.9 g) as a foam. Found: C,58.65; H,5.77; N,3.29. C19H23NO5S, 0.22 CH2Cl2 requires C,58.28; H,5.96; N,3.53%.

Workup

  1. temperatureheating for another 8 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was chromatographed on silica using 5:95 methanol

Sources & evidence

ORD record
ord-ef70fb36795b41c5b74b34fc73574e79
Source dataset
uspto-grants-2000_06
Patent number
US06071938

Reaction notes

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