Sodium Hydroxide → HCID 67175243, compound

HRID 1256108Notes

Reaction equation

HRID 1256108 reaction equation
[F:1][C:2]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(=O)C(F)(F)F)=[CH:18][C:17]=2[CH2:29][C:30]([O:32]C)=[O:31])(=[O:15])=[O:14])=[CH:10][C:5]2[B:6]([OH:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO.O>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:13](=[O:14])(=[O:15])[NH:12][C:11]2[C:2]([F:1])=[CH:3][C:4]3[CH2:8][O:7][B:6]([OH:9])[C:5]=3[CH:10]=2)=[C:17]([CH2:29][C:30]([OH:32])=[O:31])[CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86655215HCID 86655215, compound

Product 1

HCID 67175243HCID 67175243, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 2-(2-(N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (250 mg, 0.51 mmol) in 10 mL of MeOH and water (1:1, v/v) was added NaOH (1N solution, 2 mL, 2.0 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 a white powder (142 mg, yield 75%). MS calcd for (C15H14BFN2O6S): 380.1. MS found (ESI negative): (M−H)−=379.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.58 (s, 1H), 7.65 (d, J=8 Hz, 1H), 7.32 (d, J=8.8 Hz, 1H), 7.17 (d, J=10.4 Hz, 1H), 6.44 (d, J=2 Hz, 2H), 6.36 (dd, J=8.8, 2 Hz, 1H), 4.88 (s, 2H), 3.89 (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-584f0168c707485da44ae3ebcfafc491
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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