Ethyl Acetate → HCID 9982364, compound

HRID 2219268Notes

Reaction equation

HRID 2219268 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@:11]([CH3:18])([CH:13]([O:16][CH3:17])[O:14][CH3:15])[C@@H:10]([OH:19])[C@H:9]([N:20]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH2:21][C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:8]=2[CH:35]=1)([O-])=O.[BH4-].[Na+].C(OCC)(=O)C>CO.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@:11]([CH3:18])([CH:13]([O:14][CH3:15])[O:16][CH3:17])[C@@H:10]([OH:19])[C@H:9]([N:20]([C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[CH2:21][C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:8]=2[CH:35]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 10311369HCID 10311369, compound

Product 1

HCID 9982364HCID 9982364, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

(2S,3S,4R)-6-nitro-4-[N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran obtained in the example 1 (100 mg, 0.2 mmol) was dissolved in methanol (2 ml), thereto Cu(OAc)2 aqueous solution (0.38 ml, 0.4 M aqueous solution, 0.15 mmol) was added. Sodium borohydride (NaBH4) (113 mg, 3.0 mmol) was slowly added to the solution for 30 min at room temperature, the reaction mixture was stirred for 1 hours, thereafter ethyl acetate (5 ml) was added to the reaction mixture. The resulting mixture was filtered to remove precipitated black solid. Saturated NaHCO3 aqueous solution (5 ml) was added to the filtrate, and extracted with ethyl acetate (30 ml). The organic layer was washed with saturated brine solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:3), to give desired compound, the compound that R1 is substituted to amino group (62 mg, yield: 67%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customto remove
  3. customprecipitated black solid
  4. additionSaturated NaHCO3 aqueous solution (5 ml) was added to the filtrate
  5. extractionextracted with ethyl acetate (30 ml)
  6. washThe organic layer was washed with saturated brine solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-033143825ebc475d9c83042dc7e80241
Source dataset
uspto-grants-2008_08
Patent number
US07414068B2

Reaction notes

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