Water → HCID 68549471, compound

HRID 2189946Notes

Reaction equation

HRID 2189946 reaction equation
[C:1]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].Cl[CH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].O>C1COCC1>[C:1]([N:8]([CH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])[NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 702953-ChloropropiophenoneHCID 85431Di-tert-butyl bicarbamate

Product 1

HCID 68549471HCID 68549471, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of di-Boc-hydrazine (2.0 g, 8.6 mmol) in THF (30 mL) was slowly added sodium hydride (210 mg, 8.6 mmol). After stirring at 0° C. for 5 minutes and then at room temperature for 30 minutes, the mixture was added to a solution of 3-chloro-1-phenylpropan-1-one (1.50 g, 8.6 mmol) in THF (10 mL). After stirring at room temperature for 30 minutes, water was added, and the mixture was partitioned between brine and ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed (15% ethyl acetate in hexanes) to provide the crude product.

Workup

  1. waitat room temperature for 30 minutes
  2. stirringAfter stirring at room temperature for 30 minutes
  3. customthe mixture was partitioned between brine and ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cfab1d87dc2c4ff2b6999de9b3b4a6ee
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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