Cesium carbonate → HCID 10248693, compound

HRID 749068Notes

Reaction equation

HRID 749068 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([O:17][C:18]([NH:20][C:21]1[C:22](=[O:28])[NH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[CH2:10]([O:17][C:18]([NH:20][C:21]1[C:22](=[O:28])[N:23]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 100838403-benzyloxycarbonylamino-6-methyl-2-pyridinone

Product 1

HCID 10248693HCID 10248693, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl bromoacetate (3.9 g, 20 mmol) was added to a stirred suspension of 3-benzyloxycarbonylamino-6-methyl-2-pyridinone (5.15 g, 20 mmol), as prepared in the preceding step, and Cs2CO3 (6.5 g, 20 mmol) in N,N-dimethylformamide (50 mL) and stirred at 40° C. overnight. The solid was removed by filtration and the filtrate concentrated under high vacuum. The residue was dissolved in ethyl acetate (150 mL), washed with water (2×50 mL), brine (50 mL), dried over Na2SO4 and concentrated in vacuo. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (25% ethyl acetate in hexane) to give the title compound as a white crystalline solid (4.2 g, 56%). 1H-NMR (300 MHz, CDCl3) δ 7.95 (d, J=7.3 Hz, 1H), 7.76 (s, 1H), 7.37 (m, 5H), 6.09 (d, J=7.6 Hz, 1H), 5.19 (s, 2H), 4.75 (s, 2H), 2.32 (s, 3H), 1.47 (s, 9H).

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate concentrated under high vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  4. washwashed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customAfter evaporating the solvent in vacuo
  8. customthe residue was purified by flash column chromatography (25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6b1ccdafb89c4b188f736a0586c7e6bf
Source dataset
uspto-grants-2008_07
Patent number
US07402586B2

Reaction notes

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