Lithium Hydroxide → HCID 59364295, compound

HRID 1810119Notes

Reaction equation

HRID 1810119 reaction equation
[C:1]1([CH3:41])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=4)[N:21](S(C4C=CC(C)=CC=4)(=O)=O)[CH:20]=3)=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.CO.O>[C:1]1([CH3:41])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=4)[NH:21][CH:20]=3)=[CH:11]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59364223HCID 59364223, compound

Product 1

HCID 59364295HCID 59364295, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 223 (0.2 g, 0.34 mmol) in THF/MeOH/H2O (5:5:1) was added LiOH (0.052 g, 2.2 mmol) (Scheme 16). The reaction mixture was stirred at 50° C. for 0.5 h. The solution was cooled to room temperature and concentrated. Water (10 mL) was added and pH was adjusted to 7 with 1N HCl. The aqueous phase was extracted with ethyl acetate (3×10mL). The combined organic phase was dried with MgSO4, and the solvent was removed in vacuo. The residue was purified by flash chromatography (ethyl acetate/hexane, 1:1, V:V) to yield QR-0170 (0.13 g, 89%), 1H NMR (DMSO): 2.30 (s, 3H), 7.33-7.39 (m, 3H), 7.45 (t, 1H, J=7.6), 7.66 (d, 1H, J=9.0), 7.80 (d, 1H, J=7.8), 7.96 (d, 2H, J=8.3), 8.06-8.10 (m, 3H), 8.13 (s, 1H), 8.60 (d, 1H, J=1.7), 12.18 (s, 1H); 13C NMR (DMSO): 21.49, 109.45, 112.89, 114.04, 116.56, 116.89, 117.64, 121.21, 123.24, 124.33, 125.48, 125.78, 127.29, 128.41, 129.84, 130.71, 134.52, 135.20, 139.97, 141.60, 146.03.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated
  3. additionWater (10 mL) was added
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×10mL)
  5. dry with materialThe combined organic phase was dried with MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography (ethyl acetate/hexane, 1:1, V:V)

Sources & evidence

ORD record
ord-6e92cd5b9b4c4cfeba4e4c792a1d20d2
Source dataset
uspto-grants-2013_01
Patent number
US08362066B2

Reaction notes

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