Methanol → HCID 67335518, compound

HRID 2102236Notes

Reaction equation

HRID 2102236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68983278HCID 68983278, compound

Product 1

HCID 67335518HCID 67335518, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step C (Isomer A, 0.99 g, 2.13 mmol) in THF (30 mL) was added methanol (10 mL) followed by sodium hydroxide solution (2N, 2 mL, 4 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to remove the organic solvents. The residue was acidified with 1N HCl until the pH was less than 2. The resulting solution was extracted with ethyl acetate (3×) dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound as a white solid. This material was used in the next step without any further purification. 1H NMR (DMSO, 500 MHz): δ 7.89(d, J=8.2 Hz, 2H), 7.88(d, J=1.8 Hz, 2H), 7.55(d, J=1.9 Hz, 1H), 7.38(d, J=8.7 Hz, 2H), 7.15(d, J=8.3 Hz, 2H), 7.11(s, 1H), 7.04(d, J=8.7 Hz, 2H), 5.5(s, 2H), 3.79(s, 3H). LC-MS: 2.69 min. (M+H)=453.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove the organic solvents
  3. extractionThe resulting solution was extracted with ethyl acetate (3×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-641f4d83e2d845a18536cc081f05249e
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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