Ethyl Acetate → HCID 67173706, compound

HRID 1256181Notes

Reaction equation

HRID 1256181 reaction equation
[F:1][C:2]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=2[NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])(=[O:15])=[O:14])=[CH:10][C:5]2[B:6]([OH:9])[O:7][CH2:8][C:4]=2[CH:3]=1.CCOC(C)=O.[H][H]>CO.[Pd]>[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]([NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])[CH:18]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67174655HCID 67174655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67173706HCID 67173706, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ethyl 2-(N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-nitrophenylcarbamate (0.15 g, 0.34 mmol) in 10 mL of MeOH: EtOAc was added Pd/C (10 wt. % on activated carbon, 50 mg), followed by charging with hydrogen under 50 psi for 2 hour. The crude was filtered through celite, concentrated, the residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound ethyl 5-amino-2-(N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenylcarbamate as light yellow solid (114 mg). MS calcd for (C16H17BFN3O6S): 409.1. MS found (ESI negative): (M−H)−=408.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.84 (s, 1H), 9.30 (s, 1H), 8.49 (s, 1H), 7.65 (d, J=8 Hz, 1H), 7.24 (m, 2H), 7.20 (d, J=10 Hz, 1H), 6.18 (dd, J=8.8, 2 Hz, 1H), 6.09 (bs, 2H), 4.89 (s, 2H), 4.01 (q, J=7.2 Hz, 2H), 1.17 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationThe crude was filtered through celite
  2. concentrationconcentrated
  3. customthe residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-65ea80ec5b9340dfbcdee5613ea85288
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…