Acetone → HCID 22464055, compound

HRID 1935624Notes

Reaction equation

HRID 1935624 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH2:5]2.[CH3:15][C:16]([CH3:18])=O.[C:19]([O-:22])([OH:21])=O.[Na+].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O>[CH2:15]([O:21][C:19]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH2:5]2)=[O:22])[C:16]1[CH:18]=[CH:9][CH:10]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 22464070HCID 22464070, compound

Product 1

HCID 22464055HCID 22464055, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of the product from Step 2 (7.39 g, 0.0044 mol), acetone (130 ml), water (130 ml) and NaHCO3 (12 g, 0.143 mol) is cooled, under nitrogen in an ice bath and treated, dropwise stirring 10 min, with benzyl chloroformate (14.42 ml). It is kept in the ice bath for 20 min and at ambient temperature for 3.5 h and concentrated to remove acetone. The resulting solid is collected by filtration, washed with water, dried and recrystallized from EtOAc (Darco) to give 8.23 g of the titled product.

Workup

  1. temperatureis cooled, under nitrogen in an ice bath
  2. additiontreated
  3. concentrationconcentrated
  4. customto remove acetone
  5. filtrationThe resulting solid is collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from EtOAc (Darco)

Sources & evidence

ORD record
ord-56ee21ebd05a40bab23812b03f538a45
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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