Trifluoroacetic acid → N-[2-[[[[(1R,2S,5R)-7-Oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl]amino]oxy]ethyl]sulfamide

HRID 2400648Notes

Reaction equation

C(OC(=O)[NH:7][S:8](=[O:31])(=[O:30])[NH:9][CH2:10][CH2:11][O:12][NH:13][C:14]([C@@H:16]1[CH2:22][CH2:21][C@@H:20]2[CH2:23][N:17]1[C:18](=[O:29])[N:19]2[O:24][S:25]([OH:28])(=[O:27])=[O:26])=[O:15])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:29]=[C:18]1[N:17]2[CH2:23][C@@H:20]([CH2:21][CH2:22][C@H:16]2[C:14]([NH:13][O:12][CH2:11][CH2:10][NH:9][S:8](=[O:30])(=[O:31])[NH2:7])=[O:15])[N:19]1[O:24][S:25]([OH:28])(=[O:26])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of tert-butyl({2-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}sulfamoyl)carbamate 81 (0.20 g, 0.40 mmol) in DCM (5.0 mL) was added trifluoroacetic acid (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 0.5 h and at room temperature for 2 h, concentrated and washed with ether. The white solid was collected by centrifugation. The crude product was purified by preparative HPLC to provide

Workup

concentrationconcentrated
washwashed with ether
customThe white solid was collected by centrifugation
customThe crude product was purified by preparative HPLC
customto provide

Sources & evidence

ORD record: ord-3183ae953ea145379e00e2c569d701e8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796257B2

Reaction notes

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