Potassium Carbonate → HCID 21072863, compound

HRID 1867317Notes

Reaction equation

HRID 1867317 reaction equation
[C:1]([C:4]1[C:5]([OH:25])=[C:6]([NH:18][C:19](=[O:24])[C:20](Br)([CH3:22])[CH3:21])[CH:7]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:4]1[C:5]2[O:25][C:20]([CH3:22])([CH3:21])[C:19](=[O:24])[NH:18][C:6]=2[CH:7]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21072865N-(3-acetyl-5-benzyloxy-2-hydroxyphenyl)-2-bromo-2-methylpropionamide

Product 1

HCID 21072863HCID 21072863, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.60 g (16.2 mmol) of N-(3-acetyl-5-benzyloxy-2-hydroxyphenyl)-2-bromo-2-methylpropionamide and 2.76 g (20 mmol) of potassium carbonate are stirred for 1 hour in 70 mL acetonitrile at reflux temperature. The solid is suction filtered, the filtrate is evaporated down, and the residue is combined with 30 mL of ethyl acetate. After fresh filtration and distilling off the solvent, the crude product is crystallized from a little methanol. Yield: 1.00 g (19%); mass spectroscopy [M+H]+=326; melting range=148° C.-150° C.

Workup

  1. temperatureat reflux temperature
  2. filtrationfiltered
  3. customthe filtrate is evaporated down
  4. filtrationAfter fresh filtration
  5. distillationdistilling off the solvent
  6. customthe crude product is crystallized from a little methanol

Sources & evidence

ORD record
ord-6733d131e8784ce4a5c4ed61bf3e1eb0
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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