Trifluoroacetic acid → (2S, 5R)-6-sulfooxy-2-(aminomethyl)-7-oxo-1,6-diaza-bicyclo [3.2.1]octane

HRID 57334

Reaction equation

HRID 57334 reaction equation
FC(F)(F)C(O)=O.[S:8]([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][CH:14]1[CH2:15][CH2:16][CH:17]2[CH2:22][NH2:23])([OH:11])(=[O:10])=[O:9]>C(O)(C)C.O>[S:8]([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[CH2:22][NH2:23])([OH:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1180111186-Sulfooxy-2-(amino methyl)-7-oxo-1,6-diazabicyclo[3.2.1]octane

Product 1

HCID 91669185(2S, 5R)-6-sulfooxy-2-(aminomethyl)-7-oxo-1,6-diaza-bicyclo [3.2.1]octane

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

The compound of Formula (IX) was reacted with trifluoroacetic acid in a suitable solvent such as dichloromethane to provide trifluoroacetic acid and sodium salt of 6-sulfooxy-2-(amino methyl)-7-oxo-1,6-diazabicyclo[3.2.1]octane (X). This trifluoroacetic acid and sodium salt (X) was further treated with water isopropyl alcohol mixture to obtain zwitterion form, (2S, 5R)-6-sulfooxy-2-(aminomethyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane (XI).

Sources & evidence

ORD record
ord-d88982eb8b204e5e946a4513e5966aca
Source dataset
uspto-grants-2016_09
Patent number
US09434728B1

Linked notes

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