Sodium Hydroxide → HCID 18189006, compound

HRID 1358145Notes

Reaction equation

HRID 1358145 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][C:6]=1[CH:7]([C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH:16]=[CH:17][CH:18]=1)[O:8]2.[OH-].[Na+]>CO.O.Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][C:6]=1[CH:7]([C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:16]=[CH:17][CH:18]=1)[O:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70026102HCID 70026102, compound

Product 1

HCID 18189006HCID 18189006, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of Example 150 (0.78 g, 1.6 mmol) and NaOH (0.67 g, 16.7 mmol) in MeOH-H2O (3 mL, 1:1) was stirred for 6 hours, diluted with aqueous HCl (50 mL, 1M) and extracted with ethyl acetate (3×35 mL). The combined ethyl acetate was dried (MgSO4), filtered and concentrated under reduced pressure to provide the titled compound (0.76 g, 99%) of the title compound. 1NMR (CDCl3 300 MHz) δ 1.95 (quintet, J=7 Hz, 2H), 2.31 (t, J=7 Hz, 2H), 2.68 (t, J=7 Hz, 2H), 2.95 (s, 3H), 3.94 (s, 3H), 5.93 (s, 1H), 6.55 (d, J=3 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 6.69 (dd, J=2 Hz, 8 Hz, 1H), 6.89 (s, 1H), 7.15 (t, J=8 Hz, 1H), 7.15-7.24 (m, 3H), 7.25-7.32 (m, 4H), 8.42 (d, J=9 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×35 mL)
  2. dry with materialThe combined ethyl acetate was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e142b784d3d492ca73f7ce6430ea39e
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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