Ethyl ketone → HCID 70138339, compound

HRID 377046Notes

Reaction equation

HRID 377046 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][C:9]=1[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])([CH3:4])([CH3:3])[CH3:2].[CH3:25][CH2:26][C:27](=O)[CH2:28][CH3:29].S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13]([NH:14][CH:27]([CH2:28][CH3:29])[CH2:26][CH3:25])=[CH:12][CH:11]=[CH:10][C:9]=1[C:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=1[CH3:21])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7288Ethyl ketoneHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 54228684HCID 54228684, compound

Product 1

HCID 70138339HCID 70138339, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere was combined 5 ml of acetic acid, 205 mg (0.62 mmol) of the title compound of Example 4 and 126 μl (1.25 mmol) of 3-pentanone, followed by 890 mg (6.29 mmol) of powdered sodium sulfate (Na2SO4). The solution was allowed to stir for 20 minutes, at which point 158 mg (0.75 mmol) of sodium triacetoxyborohydride (NaBH(OAc)3) was added. The solution was allowed to stir for 45 minutes and was then quenched with aqueous bicarbonate (75 ml) and was extracted with ethyl acetate (2×30 ml). The organic extract was washed with water (1×25 ml) and then brine (1×25 ml), and then dried over Na2SO4, filtered and concentrated in vacuo to afford 232 mg of crude product, which was chromatographed on silica gel using 9:1 hexane:ethyl acetate to afford 186 mg (74.7%) of the title compound.

Workup

  1. additionwas added
  2. customwas then quenched with aqueous bicarbonate (75 ml)
  3. extractionwas extracted with ethyl acetate (2×30 ml)
  4. extractionThe organic extract
  5. washwas washed with water (1×25 ml)
  6. dry with materialbrine (1×25 ml), and then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford 232 mg of crude product, which
  10. customwas chromatographed on silica gel using 9:1 hexane

Sources & evidence

ORD record
ord-0c669a37769b495e8d80e52edd11cae1
Source dataset
uspto-grants-2000_02
Patent number
US06022978

Reaction notes

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