Sodium Hydroxide → HCID 16203445, compound

HRID 2189964Notes

Reaction equation

HRID 2189964 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C@@H:15]2[C:10]([C:11]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:12]=3[CH2:13][CH2:14]2)=[N:9]1)=[O:7])(=O)C.[OH-].[Na+]>CO.C(OCC)(=O)C>[OH:4][CH2:5][C:6]([N:8]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C@@H:15]2[C:10]([C:11]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:12]=3[CH2:13][CH2:14]2)=[N:9]1)=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 16204326HCID 16204326, compound

Product 1

HCID 16203445HCID 16203445, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 150 (0.150 g, 0.36 mmol) in methanol (10 mL) was added NaOH (50%, 2 mL) at room temperature. The reaction mixture was stirred at room temperature for 24 h before being diluted with ethyl acetate. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated. The residue obtained was purified by column chromatography on silica gel column using ethyl acetate-hexane (2:3) as eluent to furnish (151) (0.105 g, 78%): mp 163-64° C., 1H NMR (400 MHz, CDCl3): δ 1.06-1.17 (m, 1H), 1.72-1.78 (m, 1H), 2.76-2.89 (m, 2H), 3.76 (s, 3H), 3.87 (s, 3H), 4.55-7.70 (m, 2H), 5.66 (d, J=10.0 Hz, 1H), 6.82 (d, J=9.2 Hz, 2H), 6.92-6.95 (dd, J=2.4 and 8.8 Hz, 1H), 6.99 (d, J=9.2 Hz, 2H), 7.07 (d, J=8.4 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H). 13C NMR (400 MHz, CDCl3): δ 24.38, 28.90, 48.57, 55.46, 55.76, 61.40, 69.61, 108.02, 114.34, 119.12, 127.53, 127.84, 128.47, 130.32, 132.61, 157.67, 158.36, 159.42, 168.66. Anal. (C21H22N2O4) C, H, N.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customwas purified by column chromatography on silica gel column

Sources & evidence

ORD record
ord-95c4519682d94916b86f13ff77276666
Source dataset
uspto-grants-2012_12
Patent number
US08324262B2

Reaction notes

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