Methyl 2-(3-(4-(benzyloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate → Methyl 2-(3-(4-hydroxyphenyl)isoxazole-5-carboxamido)-3-methylbutanoate

HRID 75847Notes

Reaction equation

HRID 75847 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([C:20]([NH:22][CH:23]([CH:28]([CH3:30])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])=[O:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([C:20]([NH:22][CH:23]([CH:28]([CH3:30])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])=[O:21])[O:17][N:16]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 67355429Methyl 2-(3-(4-(benzyloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

Product 1

HCID 136337389Methyl 2-(3-(4-hydroxyphenyl)isoxazole-5-carboxamido)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To Methyl 2-(3-(4-(benzyloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate (6 g) in THF (120 ml), 10% Palladium on carbon (Wet, 600 mg) was added and hydrogenated at 50 psi for 3 hours. Reaction mixture was filtered through Celite and filtrate was concentrated to obtain yellow residue. This residue was purified by column chromatography (silica gel, EtOAc—CHCl3) to obtain yellow solid, which was crystallized using DCM—Petroleum ether to obtain the title compound as pale yellow solid. Yield: 2.25 g (48%); MS (ES+): m/z−319 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 10.01 (bs, 1H), 9.16 (d, 1H), 7.75 (d, 2H), 7.61 (s, 1H), 6.91 (d, 2H), 4.3 (m, 1H), 3.67 (s, 3H), 2.21 (m, 1H), 0.96 (d, 6H);

Workup

  1. customReaction mixture
  2. filtrationwas filtered through Celite and filtrate
  3. concentrationwas concentrated
  4. customto obtain yellow residue
  5. customThis residue was purified by column chromatography (silica gel, EtOAc—CHCl3)
  6. customto obtain yellow solid, which
  7. customwas crystallized

Sources & evidence

ORD record
ord-1ebf9d243f4b4bb5acf919dae8f076b3
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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