Potassium Carbonate → HCID 54372863, compound

HRID 1601084Notes

Reaction equation

HRID 1601084 reaction equation
[C:1]([N:8]([CH3:19])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>CC(C)=O>[C:1]([N:8]([CH3:19])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[CH:14][CH:13]=1)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 53676914HCID 53676914, compound

Product 1

HCID 54372863HCID 54372863, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-[2-(BOC-methylamino)acetyl]phenol (5.04 g, 19.0 mmol) and K2CO3 (2.63 g, 19.0 mmol) in acetone (100 mL) was stirred at reflux under argon for 1 h. The mixture was cooled to RT and benzyl bromoacetate (5.23 g, 22.8 mmol) was added. The reaction was heated at reflux for 18 h, then was cooled and filtered. The filter cake was washed with acetone, and the filtrate was concentrated on the rotavap. The residue was dissolved in CH2Cl2 (300 mL) and washed sequentially with H2O (50 mL) and brine (50 mL). Drying (Na2SO4), concentration, and flash chromatography (silica gel, 1:3 EtOAc/hexanes) yielded the title compound (7.28 g, 93%): 1H NMR (250 MHz, CDCl3) δ 6.85-7.95 (m, 9 H), 5.23 (s, 2H), 4.71 (s, 2H), 4.55 (d, 2H), 2.95 (d, 3H), 1.45 (d, 9H).

Workup

  1. temperatureat reflux under argon for 1 h
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 18 h
  4. temperaturewas cooled
  5. filtrationfiltered
  6. washThe filter cake was washed with acetone
  7. concentrationthe filtrate was concentrated on the rotavap
  8. dissolutionThe residue was dissolved in CH2Cl2 (300 mL)
  9. washwashed sequentially with H2O (50 mL) and brine (50 mL)
  10. customDrying
  11. concentration(Na2SO4), concentration, and flash chromatography (silica gel, 1:3 EtOAc/hexanes)

Sources & evidence

ORD record
ord-d12601f2146a4127b19338c646fe6b95
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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