Reaction equation
C([N:5]([CH2:9][CH2:10][O:11][NH:12][C:13]([C@@H:15]1[CH2:21][CH2:20][C@@H:19]2[CH2:22][N:16]1[C:17](=[O:28])[N:18]2[O:23][S:24]([OH:27])(=[O:26])=[O:25])=[O:14])C(=O)[O-])(C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC.FC(F)(F)C(O)=O.C([O-])(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>C(Cl)Cl.C(OCC)C>[NH2:5][CH2:9][CH2:10][O:11][NH:12][C:13]([C@@H:15]1[CH2:21][CH2:20][C@@H:19]2[CH2:22][N:16]1[C:17](=[O:28])[N:18]2[O:23][S:24]([OH:27])(=[O:26])=[O:25])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of tetrabutylammonium tert-butyl{2-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate (68.9 g, 104 mmol) in methylene chloride (170 mL) solution was cooled to −20° C., and trifluoroacetic acid (170 mL) was added at −15° C. or less over 20 min., followed by stirring at 0° C. for 35 min. To the reaction solution was added diethyl ether (510 mL), and followed by stirring at 0° C. for 40 min. The precipitated solid was filtered through Kiriyama funnel, and washed with diethyl ether (450 mL), subsequently dried under vacuo to afford a crude product (39.5 g). This was added to 0.5M sodium acetate/acetic acid buffer (400 mL, pH 5.6), and further pH was adjusted to pH 5.6 with 5M sodium hydroxide aqueous solution, and then was purified by octadecyl silica gel column chromatography (water) to afford 24.8 g of the title compound (yield 74%). Instrumental data were consistent with those of Example 59.
Workup
- stirringby stirring at 0° C. for 40 min
- filtrationThe precipitated solid was filtered through Kiriyama funnel
- washwashed with diethyl ether (450 mL)
- customsubsequently dried under vacuo
- customto afford a crude product (39.5 g)
- customwas purified by octadecyl silica gel column chromatography (water)
Sources & evidence
- ORD record
- ord-84abc51454da46e78ddd682f5e767afa
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181250B2
Linked notes
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