Water → HCID 86655219, compound

HRID 1256133Notes

Reaction equation

HRID 1256133 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)[CH:7]=1.Cl.[CH3:27][O:28][NH2:29].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[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]([NH:29][O:28][CH3:27])=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 521874O-Methylhydroxylamine hydrochlorideHCID 2724699PyBOPHCID 53234452HCID 53234452, compound

Product 1

HCID 86655219HCID 86655219, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (430 mg, 1.19 mmol) and methoxyamine hydrochloride (125 mg, 1.78 mmol) in 10 mL of DMF was added PyBOP (926 mg, 1.78 mmol) and TEA (496 uL, 3.56 mmol). The reaction mixture was stirred for 16 hours. After water was added, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated. The crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as a yellow solid (16.4 mg, yield 4%). Analytical data for title compound. MS calcd for (C16H18BN3O6S): 391.2. MS found (ESI negative): (M−H)−=390.0. 1H NMR (DMSO-d6) δ (ppm): 11.14 (s, 1H), 9.74 (s, 1H), 9.10 (bs, 1H), 7.36-7.40 (m, 2H), 7.16 (d, J=8.0 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.36 (s, 1H), 6.31 (d, J=8.8 Hz, 1H), 4.80 (s, 2H), 3.58 (s, 2H), 3.56 (s, 3H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-d07b3d5efea548c1ab759b7f88dcf2a5
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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