Sodium Carbonate → 3-[(Furan-2-carbonyl)-amino]-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester

HRID 1245401Notes

Reaction equation

HRID 1245401 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].Cl.Cl.[CH3:11][O:12][C:13](=[O:41])[CH2:14][CH:15]([NH2:40])[CH:16]1[O:20][N:19]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=[C:31]([CH3:39])[CH:30]=3)=[CH:23][CH:22]=2)[CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:41])[CH2:14][CH:15]([NH:40][C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:7])[CH:16]1[O:20][N:19]=[C:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=[C:31]([CH3:39])[CH:30]=3)=[CH:25][CH:26]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 682422-Furancarbonyl chlorideHCID 696397453-Amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester di-hydrochloride salt

Product 1

HCID 696401143-[(Furan-2-carbonyl)-amino]-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Furan-2-carbonyl chloride ((0.07 g, 0.54 mmol) was added to a mixture of 3-amino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester di-hydrochloride salt (0.22 g, 0.45 mmol) from step 10e, methylene chloride (10 mL) and aqueous sodium carbonate (5 mL) under a nitrogen atmosphere at room temperature. The reaction was stirred vigorously for 2 h, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 3-[(furan-2-carbonyl)-amino]-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester (0.23 g, 100%) as an oil. MS found: (M+H)+=514.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a47c37ba66b440ada3cad541c3e50666
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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