HCID 53234295, compound → HCID 67173922, compound

HRID 1256114Notes

Reaction equation

HRID 1256114 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]([NH:21]C(=O)C(F)(F)F)=[CH:17][C:16]=3[CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1>[NH4+].CO>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12](=[O:13])(=[O:14])[NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[C:16]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:17]=1.[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12](=[O:13])(=[O:14])[NH:11][C:8]2[CH:9]=[CH:10][C:5]3[CH2:4][O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[C:16]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:17]=1

Participants

5

Reactant 1

HCID 53234295HCID 53234295, compound

Product 2

HCID 67173922HCID 67173922, compoundYield 54%HCID 67310759HCID 67310759, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 223AmmoniumSolventHCID 887MethanolSolvent

Procedure

A solution of ethyl 3-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)propanoate (50 mg, 0.1 mmol) in 7M ammonium in MeOH (10 mL) was stirred in a sealed tube at 50° C. for 6 hours. After concentrated, the crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give ethyl 3-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)propanoate as a white solid (22 mg, yield 54%) and methyl 3-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)propanoate as a white solid (7.3 mg, 19%).

Workup

  1. concentrationAfter concentrated
  2. customthe crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-25ca25ca81094da89d68735486be7295
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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