Azane;hydrate → 2-(5-Amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide

HRID 1256115Notes

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][C:29]([O:31]C)=O)(=[O:14])=[O:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1.[NH3:33].O>CO>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12](=[O:14])(=[O:13])[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][C:29]([NH2:33])=[O:31])[CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 2-(2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (0.5 g, 0.001 mol) and aq. NH3.H2O (28%, 10 mL) in CH3OH was stirred at 50° C. over night. The mixture was concentrated and the residue dissolved in ethyl acetate and washed with brine, dried and concentrated, purified by column chromatography (PE:EA 5:1˜1:3) to give the title compound, which was dissolved in MeCN, acidified with aq. HCl and freeze-dried to give the product as hydrochloride salt (200 mg, yield 53%). 1HNMR DMSO-d6 400 MH. δ9.85 (s, 1H), 9.17 (s, 1H), 7.43-6.32 (m, 6H), 5.92 (s, 2H), 4.86 (s, 2H), 3.74 (s, 2H). LC-MS m/z 360 (M−H, negative); HPLC purity: 96.93% (220 nm), 99.27% (254 nm).

Workup

concentrationThe mixture was concentrated
dissolutionthe residue dissolved in ethyl acetate
washwashed with brine
customdried
concentrationconcentrated
custompurified by column chromatography (PE:EA 5:1˜1:3)

Sources & evidence

ORD record: ord-273667dedd1348bca67f8d4c3ac9fb07
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461134B2

Reaction notes

Loading…