Water → HCID 53234456, compound

HRID 1256112Notes

Reaction equation

HRID 1256112 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([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:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.O.[CH:27](O)([CH3:29])[CH3:28]>S(=O)(=O)(O)O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:24])(=[O:25])[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:6]([CH2:8][C:9]([O:11][CH:27]([CH3:29])[CH3:28])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 53234452HCID 53234452, compound

Product 1

HCID 53234456HCID 53234456, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (0.5 g, 1.38 mmol) in isopropanol (100 mL) was added 4 drops of concentrated sulfuric acid. The reaction was heated to reflux for 48 hrs then cooled to room temperature and added to 10 mL of water before evaporating all solvent under vacuum. The residue was partitioned between ethyl acetate and 1M HCl and the organic layer dried over Na2SO4. Removal of solvent under vacuum provided 357 mg (64%) of the title compound as a white solid. MS calcd for (C18H2O3N2O6S): 404.1. MS found (ESI negative): (M−H)−=403.1. 1H NMR (DMSO-d6) δ (ppm): 9.84 (s, 1H), 9.15 (s, 1H), 7.40-7.47 (m, 2H), 7.19 (d, J=8.4, 1H), 7.10 (d, J=2.0 Hz, 1H), 6.37 (bs, 2H), 5.91 (bs, 2H), 4.85 (m, 3H), 3.83 (s, 1H), 1.16 (d, J=6.4, 6H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 48 hrs
  3. custombefore evaporating all solvent under vacuum
  4. customThe residue was partitioned between ethyl acetate and 1M HCl
  5. dry with materialthe organic layer dried over Na2SO4
  6. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-3e52bd9da92e4495b51ced080c8474b3
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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