Sodium Hydroxide → HCID 53234452, compound

HRID 1256107Notes

Reaction equation

HRID 1256107 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21]C(=O)C(F)(F)F)=[CH:17][C:16]=3[CH2:28][C:29]([O:31]C)=[O:30])(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.[OH-].[Na+]>CO.O>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12](=[O:13])(=[O:14])[NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[C:16]([CH2:28][C:29]([OH:31])=[O:30])[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86655206Methyl 2-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate

Product 1

HCID 53234452HCID 53234452, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 2-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (134 mg, 0.28 mmol) in 2 mL of MeOH and water (1:1, v/v) was added NaOH (34 mg, 0.85 mmol). The reaction mixture was stirred at room temperature for 16 hours. After MeOH was removed in vacuo, the residue was dissolved in water and acidified with 0.5N HCl. The mixture was extracted with ethyl acetate three times, and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound as an off-white solid (51 mg, yield 50%). MS calcd for (C15H15BN2O6S): 362.1. MS found (ESI negative): (M−H)−=361.1. 1H NMR (DMSO-d6) δ (ppm): 9.78 (s, 1H), 9.10 (bs, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.35 (s, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.04 (d, J=8.0 Hz, 1H), 6.34 (s, 1H), 6.32 (d, J=8.8 Hz, 1H), 4.79 (s, 2H), 3.73 (s, 2H).

Workup

  1. customAfter MeOH was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-554979fcb9b7444b8eebd839de23649c
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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