Lithium Hydroxide → HCID 15982714, compound

HRID 749024Notes

Reaction equation

HRID 749024 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([C:31](=[O:35])[N:32]([CH3:34])[CH3:33])[NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[CH3:34][N:32]([CH3:33])[C:31]([CH:19]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:22])=[O:23])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:7][CH:8]=2)=[CH:17][CH:16]=1)=[O:35]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69113286HCID 69113286, compound

Product 1

HCID 15982714HCID 15982714, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The sulfonamide compound 54 (1.1 g, 2.06 mmol) was dissolved in THF (30 mL) and diluted with water (30 mL). Lithium hydroxide (0.2 g, 8.26 mmol) was added and the reaction mixture was stirred at room temperature for about 2 h. The THF was evaporated and the resulting aqueous layer was acidified with 2.0 M HCl and extracted into EtOAc (2×25 mL). The organic layer was washed with water (1×25 mL) and brine (1×25 mL), dried and concentrated to yield the desired acid compound 55 (1.05 g, 98%). 1H NMR (400 MHz, DMSO-d6): 12.2 (br, 1H), 8.09 (d, J=9.2 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.0 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.0 Hz, 2H), 4.33 (m, 1H), 2.81-2.87 (m, 3H), 2.75 (s, 3H), 2.61-2.67 (m, 1H), 2.56 (t, J=8.0 Hz, 2H), 2.53 (s, 3H), 2.27 (s, 3H).

Workup

  1. customThe THF was evaporated
  2. extractionextracted into EtOAc (2×25 mL)
  3. washThe organic layer was washed with water (1×25 mL) and brine (1×25 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4b3c0e2230c1405883b274db6c3b8d0f
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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