Ethyl Acetate → HCID 10095704, compound

HRID 1179460Notes

Reaction equation

HRID 1179460 reaction equation
[CH3:1][O:2][CH:3]([O:33][CH3:34])[C@:4]1([CH3:32])[C@@H:9]([OH:10])[C@H:8]([N:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:12][C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[C:7]2[CH:25]=[C:26]([N+:29]([O-])=O)[CH:27]=[CH:28][C:6]=2[O:5]1.[BH4-].[Na+].C(OCC)(=O)C>CO.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH2:29][C:26]1[CH:27]=[CH:28][C:6]2[O:5][C@@:4]([CH:3]([O:33][CH3:34])[O:2][CH3:1])([CH3:32])[C@@H:9]([OH:10])[C@H:8]([N:11]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[CH2:12][C:13]3[NH:14][CH:15]=[CH:16][N:17]=3)[C:7]=2[CH:25]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 9870129HCID 9870129, compound

Product 1

HCID 10095704HCID 10095704, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

To the solution of the nitro compound (177 mg, 0.36 mmol) prepared from example 1 in methanol (2 mL) was added a 0.4 M aqueous solution of Cu(OAc)2 (0.38 mL, 0.15 mmol), then slowly added sodium borohydride (113 mg, 3.0 mmol) over 30 min. The reaction mixture was stirred for an hour at room temperature, and ethyl acetate (5 mL) was added to the reaction. The black precipitates were removed by filtration, then to the filtrate was added a saturated aqueous solution of NaHCO3 (5 mL). The mixture was extracted with ethyl acetate (30 mL), and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:4) to afford the title compound (58 mg, 35%).

Workup

  1. customThe black precipitates
  2. customwere removed by filtration
  3. additionto the filtrate was added a saturated aqueous solution of NaHCO3 (5 mL)
  4. extractionThe mixture was extracted with ethyl acetate (30 mL)
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-a8c72f14fa5145519bc87185ccf57580
Source dataset
uspto-grants-2007_10
Patent number
US07279497B2

Reaction notes

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