Potassium Carbonate → Ethyl 2-Methyl-2-{4-[2-methoxy-5-chloro-benzamido-methyl]-biphenyl-4'-oxy}-propionate

HRID 596333Notes

Reaction equation

HRID 596333 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[C:34]([CH3:41])([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36].BrC(C)(C)C([O-])=O>C(C(C)=O)C>[CH3:40][C:34]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][NH:7][C:5](=[O:6])[C:4]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:3]=3[O:2][CH3:1])=[CH:14][CH:13]=2)=[CH:16][CH:17]=1)([CH3:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36]

Participants

6

Reactant 4

HCID 11430Potassium Carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 6993926alpha-BromoisobutyrateHCID 214519534-[2-Methoxy-5-chlorobenzamido-methyl]-4'-hydroxy-biphenyl

Product 1

HCID 21418525Ethyl 2-Methyl-2-{4-[2-methoxy-5-chloro-benzamido-methyl]-biphenyl-4'-oxy}-propionate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2.7 gm (7.35 millimols) of 4-[2-methoxy-5-chlorobenzamido-methyl]-4'-hydroxy-biphenyl were refluxed in 30 ml of methyl ethyl ketone with 1.26 gm (9.2 millimols) of potassium carbonate for 1 to 2 hours, and then 2.23 gm (11 millimols) of ethyl 2-bromo-2-methyl-propionate were added dropwise. After three hours, another 0.63 gm (4.6 millimols) of potassium carbonate and 0.46 gm (2.2 millimols) of 2-bromo-2-methyl-propionate were added to complete the reaction, and the mixture was heated for 3 to 4 hours more. After cooling, filtering and distilling off the solvent, the residual crude product was purified by chromatography on a silicagel column with benzene/ethyl acetate (9:1) as the eluant. The evaluation of column chromatograph was carried out by thin-layer chromatography. The fractions containing the pure product were combined, and the solvent was distilled off, yielding 1.8 gm (51% of theory) of a slightly yellow oil. M.p. < 20° C.

Workup

  1. customthe reaction
  2. temperaturethe mixture was heated for 3 to 4 hours more
  3. temperatureAfter cooling
  4. filtrationfiltering
  5. distillationdistilling off the solvent
  6. customthe residual crude product was purified by chromatography on a silicagel column with benzene/ethyl acetate (9:1) as the eluant
  7. additionThe fractions containing the pure product
  8. distillationthe solvent was distilled off
  9. customyielding 1.8 gm (51% of theory) of a slightly yellow oil

Sources & evidence

ORD record
ord-2078e6ffd8014b9dae59785fa099d242
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Reaction notes

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