Water → HCID 10043064, compound

HRID 508599Notes

Reaction equation

HRID 508599 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:17]2[CH:22]=[CH:21][C:20]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:19][CH:18]=2)[N:7]=1)=[O:5])C.[Li+].[OH-].O>C1COCC1>[C:11]1([C:9]2[N:8]([C:17]3[CH:18]=[CH:19][C:20]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:21][CH:22]=3)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 11164601HCID 11164601, compound

Product 1

HCID 10043064HCID 10043064, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 3b (0.37 g, 1 mmol) in THF (10 mL) was added LiOH (35 mg, 1.5 mmol) followed by 2 mL of water at room temperature. The reaction mixture was stirred overnight. The reaction was quenched by adding 1N HCl. The solvent was evaporated in vacuo. The resulting white solids were collected by suction filtration and washed with water. The crude product was recrystallized from MeOH to give the titled compound (0.33 g, 96% yield) as a white solid. mp 188.5-190.9° C. 1H NMR (300 MHz, DMSO-d6): δ 13.10 (s, 1H), 7.87 (d, J=8 Hz, 2H), 7.55-7.48 (m, 4H), 7.44-7.37 (m, 3H), 7.34-7.26 (m, 2H), 7.10 (s, 1H).

Workup

  1. customThe reaction was quenched
  2. additionby adding 1N HCl
  3. customThe solvent was evaporated in vacuo
  4. filtrationThe resulting white solids were collected by suction filtration
  5. washwashed with water
  6. customThe crude product was recrystallized from MeOH

Sources & evidence

ORD record
ord-22635d83bab64f4bba7a12cd73fce8da
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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