Sodium Hydroxide → HCID 9843618, compound

HRID 1375653Notes

Reaction equation

HRID 1375653 reaction equation
[OH:1][C:2]1[C:3]([C:28]([O:30][CH3:31])=[O:29])=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6]/[CH:7]=[CH:8]/[C:9]1[CH:10]=[C:11]([C:15]2[O:19][N:18]=[C:17]([C:20]([O:22]CC)=[O:21])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1.[OH-].[Na+]>C1COCC1.CO>[OH:1][C:2]1[C:3]([C:28]([O:30][CH3:31])=[O:29])=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6]/[CH:7]=[CH:8]/[C:9]1[CH:10]=[C:11]([C:15]2[O:19][N:18]=[C:17]([C:20]([OH:22])=[O:21])[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69507945HCID 69507945, compound

Product 1

HCID 9843618HCID 9843618, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of Example 1E in THF/MeOH (1:1 10 mL), was added 2N NaOH (225 μL, 0.45 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes and quenched with 1N HCl and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), filtered and concentrated to provide the titled compound. MS (ESI(+)) m/e 413 (M+18)+; 1H NMR (300 MHz, DMSO-d6) δ 9.96 (s, 1H), 8.06(s, 1H), 7.83(d, J=7.5 Hz, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.53 (t, J=7.5 Hz, 1H), 7.49(s, 1H), 7.19(t, J=8.4 Hz, 1H), 6.79 (d, J=15.9 Hz, 1H), 6.65 (dt, J1=15.9 Hz, J2=5.8 Hz, 1H), 6.61(d, J=8.4 Hz, 1H), 6.52(d, J=8.4 Hz, 1H), 4.75(d, J=5.0 Hz, 2H), 3.79 (s, 3H).

Workup

  1. customquenched with 1N HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43cc141637364b60a8e1f7d7ceda2416
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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