Methyl 3,3-dimethyl-4-pentenoate → 3-Methyl-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-butyric acid methyl ester

HRID 1245388

Reaction equation

HRID 1245388 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]([CH3:9])([CH3:8])[CH:6]=[CH2:7].[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][O:23][C:24]2[CH:32]=[CH:31][C:27]([CH:28]=[N:29][OH:30])=[CH:26][CH:25]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>>[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]([CH3:9])([CH:6]1[O:30][N:29]=[C:28]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([CH3:11])[CH:21]=3)=[CH:32][CH:31]=2)[CH2:7]1)[CH3:8]

Participants

3

Reactant 2

HCID 114129Methyl 3,3-dimethyl-4-pentenoateHCID 738530794-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime

Product 1

HCID 696397723-Methyl-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-butyric acid methyl esterYield 100%

Procedure

Following a procedure analogous to that used in Example step 1c, but using 3,3-dimethyl-pent-4-enoic acid methyl ester and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime from step 1b, the crude reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 3-methyl-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-butyric acid methyl ester (0.14 g, 100%) as a crude oil. MS found: (M+H)+=433.

Workup

  1. customthe crude reaction
  2. customwas partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b07f9fd71de443e99d9ad915d13ceec6
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Linked notes

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