Potassium Carbonate → HCID 10248693, compound

HRID 567799Notes

Reaction equation

HRID 567799 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CC(=O)CC>[CH2:12]([O:11][C:10]([NH:9][C:5]1[C:6](=[O:8])[N:7]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 100838403-benzyloxycarbonylamino-6-methyl-2-pyridinone

Product 1

HCID 10248693HCID 10248693, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A slurry of benzyl N-(6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)carbamate (preparation 3) (20 g, 78 mmol) in 2-butanone (500 ml) was treated with K2CO3 (53.9 g, 94 mmol) and further 2-butanone (100 ml). The resultant mixture was treated cautiously with tert-butyl 2-bromoacetate (15.2 ml, 94 mmol) and stirred at room temperature for 18 hr. The solvent was evaporated and the crude material was partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate, the combined organic layers washed with sat aq brine and dried over Na2SO4. Removal of the drying agent by filtration followed by evaporation of the solvent gave the crude product which was purified by recrystallisation from ethyl acetate:hexane to give the desired product (white solid, 15.1 g, 52%). 1H NMR (CDCl3) δ: 1.40 (s, 9H), 2.20 (s, 3H), 4.70 (s, 2H), 5.20 (s, 2H), 6.05 (d, 1H), 7.40 (m, 5H), 7.70 (s, br, 1H), 7.90 (d, 1H). LRMS m/z=373.6 (M+1)+.

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was partitioned between ethyl acetate and water
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe combined organic layers washed with sat aq brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the drying agent
  7. filtrationby filtration
  8. customfollowed by evaporation of the solvent
  9. customgave the crude product which
  10. customwas purified by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-489d1be9a87b48c487ee01d5fd602fa0
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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