Hydrochloric Acid → HCID 53234367, compound

HRID 1256088Notes

Reaction equation

HRID 1256088 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:8]([CH2:26][CH2:27][C:28](=[O:30])[CH3:29])[CH:7]=1)=O.O[Li].O.Cl>CO.O>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)(=[O:24])=[O:25])=[C:8]([CH2:26][CH2:27][C:28](=[O:30])[CH3:29])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86655210HCID 86655210, compound

Product 1

HCID 53234367HCID 53234367, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-(3-oxobutyl)phenyl)acetamide (2 g, 4 mmol) in MeOH (15 mL) and water (15 mL) was added LiOH.H2O (0.93 g, 22 mmol). The mixture was stirred at r.t. overnight. The reaction mixture was concentrated, the residue was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 12%-42%, 24 min), concentrated, acidified with HCl and freeze-dried to give 4-amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(3-oxobutyl)benzenesulfonamide (650 mg, yield 40%) as HCl salt. 1H NMR: (400 MHz, DMSO-d6). δ 10.00 (s, 1H), 7.40 (d, 1H), 7.21 (d, 1H), 7.11 (d, 1H), 7.09 (d, 1H), 6.36-6.33 (m, 2H), 4.84 (s, 2H), 2.97 (t, 2H), 2.61 (t, 2H), 2.06 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 12%-42%, 24 min)
  3. concentrationconcentrated
  4. customfreeze-dried

Sources & evidence

ORD record
ord-01c7a1ce822646448e838f1652fbefbb
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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