Sodium Methoxide → HCID 57501751, compound

HRID 601522Notes

Reaction equation

HRID 601522 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][C:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[S:17][C:11]=3[C:10]2=[O:26])[CH:6]=[CH:5][C:4]=1[O:27]C(=O)C(C)(C)C.C[O-].[Na+]>C(O)C>[OH:27][C:4]1[CH:5]=[CH:6][C:7]([N:9]2[CH2:14][CH2:13][C:12]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[S:17][C:11]=3[C:10]2=[O:26])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57501750HCID 57501750, compound

Product 1

HCID 57501751HCID 57501751, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2,2-dimethyl-propionic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-4-oxo-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]-phenyl ester (749 mg, 1.61 mmol) in absolute ethanol (18 mL) and add NaOMe (183.1 mg, 6.44 mmol). Allow the reaction mixture to stir for 4 h at ambient temperature. Quench the reaction mixture with 1N HCl solution. to pH=7. Add a small amount of EtOAc (15 mL) and filter the solid precipitate via vacuum filtration to give the title compound as a yellow solid (430 mg, 70%). MS (ES+) 383.3 (M+1)+. 1H NMR (CDCl3): δ 7.95 (d, J=8.8 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 6.94 (d, J=6.2 Hz, 1H), 6.93 (s, 1H), 6.80 (dd, J=8.8, 2.2 Hz, 1H), 4.07 (t, J=7.0. Hz, 2H), 3.90 (s, 3H), 3.87 (s, 3H), 3.28 (t, J=7.0 Hz, 2H).

Workup

  1. customQuench the reaction mixture with 1N HCl solution
  2. additionAdd a small amount of EtOAc (15 mL)
  3. filtrationfilter the solid precipitate
  4. filtrationvia vacuum filtration

Sources & evidence

ORD record
ord-0ec93ab7c12a4da59825e5d0185ed7be
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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