Water → Pyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner salt

HRID 1470207Notes

Reaction equation

HRID 1470207 reaction equation
FC(F)(F)C([O-])=O.OC1C=CC=CC=1/C=[N:12]\[C@@H:13]1[C:20](=[O:21])[N:19]2[CH:14]1[S:15][CH2:16][C:17]([S:34][C:35]1[S:36][CH:37]=[C:38]([C:40]3[CH:45]=[CH:44][N+:43]([CH3:46])=[CH:42][CH:41]=3)[N:39]=1)=[C:18]2[C:22]([O:24]CC1C=CC(OC)=CC=1)=[O:23].O.CS(O[C:57](=[O:73])/[C:58](/[C:63]1[N:67]=[C:66]([NH:68][P:69]([OH:72])([OH:71])=[O:70])[S:65][N:64]=1)=[N:59]\[O:60][CH2:61][CH3:62])(=O)=O.ClCCl>C(OC)(C)(C)C>[CH2:61]([O:60]/[N:59]=[C:58](/[C:63]1[N:67]=[C:66]([NH:68][P:69]([OH:71])([OH:72])=[O:70])[S:65][N:64]=1)\[C:57]([NH:12][C@@H:13]1[C:20](=[O:21])[N:19]2[C@@H:14]1[S:15][CH2:16][C:17]([S:34][C:35]1[S:36][CH:37]=[C:38]([C:40]3[CH:45]=[CH:44][N+:43]([CH3:46])=[CH:42][CH:41]=3)[N:39]=1)=[C:18]2[C:22]([O-:24])=[O:23])=[O:73])[CH3:62]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 90408899[[3-[(Z)-N-ethoxy-C-methylsulfonyloxycarbonylcarbonimidoyl]-1,2,4-thiadiazol-5-yl]amino]phosphonic acidHCID 178491529HCID 178491529, compound

Product 1

HCID 9852981Pyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner salt

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A reactor is charged with 4-(2-(((7R)-7-((Z)-(2-hydroxybenzylidene)amino)-2-(((4-methoxybenzyl)oxy)carbonyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)thio)thiazol-4-yl)-1-methylpyridin-1-ium trifluoroacetate (1 eq), water (6-9 weight % relative to the Schiff base), (Z)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic methanesulfonic anhydride (2.5 eq) and dichloromethane (1.75 mL per gram of Schiff base). The mixture is stirred for three hours at room temperature, then added to methyl tertiary butyl ether over the course of 2-3 hours, resulting in the formation of a solid. The solid is filtered and the filter cake was washed with additional methyl tertiary butyl ether. The filtered solid is deprotected using conventional methods and dried under vacuum to yield the title compound.

Workup

  1. customresulting in the formation of a solid
  2. filtrationThe solid is filtered
  3. washthe filter cake was washed with additional methyl tertiary butyl ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cb85663e5b294540a135cede2469412a
Source dataset
uspto-grants-2015_04
Patent number
US09006421B2

Reaction notes

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