methyl 3-[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]prop-2-enoate → methyl 3-[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]propanoate

HRID 1245405Notes

Reaction equation

HRID 1245405 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH:4]=[CH:5][C:6]1([C:30]([CH3:38])([CH3:37])[O:31][SiH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1>CO>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1([C:30]([CH3:38])([CH3:37])[O:31][SiH2:32][C:33]([CH3:35])([CH3:34])[CH3:36])[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1

Participants

3

Reactant 1

HCID 131725998methyl 3-[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]prop-2-enoate

Product 1

HCID 131725999methyl 3-[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from step 24d (0.24 g, 0.44 mmol) was dissolved in methanol (15 mL), degassed by bubbling nitrogen through the solution, charged with Rh/C and hydrogen gas (40 PSI), and shaken for 2 h. The reaction was filtered and concentrated to give 3-{5-(tert-butyl-dimethyl-silanyloxymethyl)-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester as a crude oil. MS found: (M+H)+=549.

Workup

  1. customdegassed
  2. customby bubbling nitrogen through the solution
  3. additioncharged with Rh/C and hydrogen gas (40 PSI)
  4. filtrationThe reaction was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-66efaaec73ae4ee19f27db11eff66381
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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