Water → HCID 67173340, compound

HRID 1256069Notes

Reaction equation

HRID 1256069 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]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=3[O:24]C)(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.C(Cl)Cl.O>B(Br)(Br)Br>[OH:24][C:16]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=1[S:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[CH2:4][O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 67171796HCID 67171796, compound

Product 1

HCID 67173340HCID 67173340, compound

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

N-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-2-methoxy-4-nitro-benzenesulfonamide (200 mg, 0.55 mmol) was dissolved in 1 M BBr3 in CH2Cl2 (5.0 mL, 5.0 mmol) and the resulting soln was stirred at rt O/N. H2O was the resulting precipitate was isolated by filtration to give the title compound as a white solid: yield; 160 mg (83%). mp 198-199° C.; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.98 (s, 1H), 10.22 (s, 1H), 9.18 (s, 1H), 7.89-7.87 (m, 1H), 7.67-7.63 (m, 2H), 7.48 (s, 1H), 7.23-7.18 (m, 2H), 4.84 (s, 2H); MS (ESI) m/z=349 (M−1, negative); HPLC purity: 95.49% (MaxPlot 200-400 nm), 95.48% (220 nm).

Workup

  1. customwas isolated by filtration

Sources & evidence

ORD record
ord-6af1bd8cac3948dfb74da98e136249c0
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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