Dimethyl Sulfate → HCID 57193874, compound

HRID 1489181Notes

Reaction equation

HRID 1489181 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:36]=[CH:35][C:18]3[O:19][C:20]([CH3:34])([CH3:33])[C@:21]([OH:32])([CH3:31])[C@H:22]([O:23][C:24]4[N:29]=[N:28][C:27]([OH:30])=[CH:26][CH:25]=4)[C:17]=3[CH:16]=2)=[N:13][N:12]=[N:11]1)=[O:5])[CH3:2].S(OC)(O[CH3:41])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:36]=[CH:35][C:18]3[O:19][C:20]([CH3:34])([CH3:33])[C@:21]([OH:32])([CH3:31])[C@H:22]([O:23][C:24]4[CH:25]=[CH:26][C:27](=[O:30])[N:28]([CH3:41])[N:29]=4)[C:17]=3[CH:16]=2)=[N:13][N:12]=[N:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178471467HCID 178471467, compound

Product 1

HCID 57193874HCID 57193874, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture containing (3S,4R)-3,4-dihydro-6-(1-[4-ethoxycarbonylbut-1-yl]-1H-tetrazol-5-yl)-3-hydroxy-4-(3-hydroxypyridazin-6-yl)oxy-2,2,3-trimethyl-2H-benzo[b]pyran (see Example 11) (0.25 g), dimethyl sulfate (0.34 ml), anhydrous potassium carbonate (0.51 g) and acetone (10 ml) was heated under reflux for 4 hours. On cooling to room temperature the mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (50 ml) and water (50 ml).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationwas concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate (50 ml) and water (50 ml)

Sources & evidence

ORD record
ord-5726436ff9cf4c37b541c1ebe8be300f
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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