Water → HCID 67350623, compound

HRID 910581Notes

Reaction equation

HRID 910581 reaction equation
[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][NH:11][C:12]=1[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:24][C:25](ON1C(=O)CCC1=O)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C(OCC)(=O)C>CN(C)C=O>[CH2:17]([O:24][C:25]([N:11]1[C:12]([CH:13]([CH3:14])[CH3:15])=[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:16])[NH:10]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 83172Benzyl succinimido carbonateHCID 673516914-Benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one

Product 1

HCID 67350623HCID 67350623, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-Benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (2.00 g) was dissolved in N,N-dimethylformamide (5 mL) at room temperature. N-(Benzyloxycarbonyloxy)succinimide (2.42 g) was added to the solution. The mixture was heated to 50° C. and then stirred for 16 hours. After the addition of water (20 mL) and ethyl acetate (20 mL) to the reaction mixture, the aqueous layer was separated, and the organic layer was washed with water. The obtained organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate/dichloromethane=1/3 to 1/1) to give 1-benzyloxycarbonyl-4-benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (1.15 g).

Workup

  1. customthe aqueous layer was separated
  2. washthe organic layer was washed with water
  3. concentrationThe obtained organic layer was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/dichloromethane=1/3 to 1/1)

Sources & evidence

ORD record
ord-16a0481e1f3b4006939cdd3a796770e7
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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