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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 2400648
Notes
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Reaction equation

HRID 2400648 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699603HCID 86699603, compound

Product 1

HCID 86693965N-[2-[[[[(1R,2S,5R)-7-Oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl]amino]oxy]ethyl]sulfamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. concentrationconcentrated
  2. washwashed with ether
  3. customThe white solid was collected by centrifugation
  4. customThe crude product was purified by preparative HPLC
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes