Acetone → Methyl 2-(3-(4-(4-fluorobenzyloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

HRID 75848Notes

Reaction equation

HRID 75848 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.CC(C)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1>O>[F:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:12]=[C:11]([C:13]([NH:15][CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19][CH3:20])=[O:18])=[O:14])[O:10][N:9]=3)=[CH:4][CH:3]=2)=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 136337389Methyl 2-(3-(4-hydroxyphenyl)isoxazole-5-carboxamido)-3-methylbutanoate

Product 1

HCID 67353023Methyl 2-(3-(4-(4-fluorobenzyloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl 2-(3-(4-hydroxyphenyl)isoxazole-5-carboxamido)-3-methylbutanoate (150 mg) in, acetone (3 ml), potassium carbonate (78 mg) was added and stirred. To this 1-(bromomethyl)-4-fluorobenzene (0.07 ml) was added and the reaction mixture was refluxed for 2 hours and then cooled reaction. The mixture was filtered and filtrate was concentrated to obtain pale brown residue. To this residue, water was added and extracted with EtOAc. Organic layer was collected and dried over Na2SO4 and concentrated to obtain off white solid, which was crystallized using DCM-Petroleum ether to obtain the title compound as white solid. Yield: 170 (84%); MS (ES+): m/z 427 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 9.18 (d, 1H), 7.88 (d, 2H), 7.68 (s, 1H), 7.53 (m, 2H), 7.23 (m, 2H), 7.18 (d, 2H), 5.17 (s, 2H), 4.31 (m, 1H), 3.67 (s, 3H), 2.22 (m, 1H), 0.96 (d, 6H).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customreaction
  4. filtrationThe mixture was filtered
  5. concentrationfiltrate was concentrated
  6. customto obtain pale brown residue
  7. extractionextracted with EtOAc
  8. customOrganic layer was collected
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customto obtain off white solid, which
  12. customwas crystallized

Sources & evidence

ORD record
ord-e6f142c285924fecbb0a962c5b3f6330
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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