Trifluoroacetic acid → trans-sulfuric acid mono-[2-(N'-[(R)-pyrrolidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]oct-6-yl]ester

HRID 68359Notes

Reaction equation

HRID 68359 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([NH:15][NH:16][C:17]([C@H:19]2[CH2:25][CH2:24][C@@H:23]3[CH2:26][N:20]2[C:21](=[O:32])[N:22]3[O:27][S:28]([OH:31])(=[O:30])=[O:29])=[O:18])=[O:14])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([NH:15][NH:16][C:17]([C@H:19]2[CH2:25][CH2:24][C@@H:23]3[CH2:26][N:20]2[C:21](=[O:32])[N:22]3[O:27][S:28](=[O:30])(=[O:29])[OH:31])=[O:18])=[O:14])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731812trans-3-[N'-(6-sulfooxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester

Product 1

HCID 131731811trans-sulfuric acid mono-[2-(N'-[(R)-pyrrolidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]oct-6-yl]ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By using the procedure described in Step-4 of Example-1, and by using tetrabutylammonium salt of trans-3-[N′-(6-sulfooxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester (15 gm, 0.021 mmol), dichloromethane (37 ml) and trifluoroacetic acid (37 nil) to provide the title compound in 7.7 gm quantity as a white solid.

Sources & evidence

ORD record
ord-2daa51604c094a8bb30ac18579a07385
Source dataset
uspto-grants-2014_09
Patent number
US08822450B2

Reaction notes

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