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Water → Ceftobiprole

HRID 1470208
Notes
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Reaction equation

HRID 1470208 reaction equation
COC1C=CC(C[CH:8]2[S:15][CH:14]3[N:11]([C:12](=[O:25])[C@H:13]3/[N:16]=C\C3C=CC=CC=3O)[C:10]([C:26]([O-:28])=[O:27])=[C:9]2/[CH:29]=[C:30]2/[C:31](=[O:47])[N:32]([C@@H:35]3[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36]3)[CH2:33][CH2:34]/2)=CC=1.O.CS([O:55][C:56](=O)/[C:57](/[C:69]1[N:73]=[C:72]([NH2:74])[S:71][N:70]=1)=[N:58]\[O:59]CC1C=CC(OC)=CC=1)(=O)=O.ClCCl>C(OC)(C)(C)C>[NH2:74][C:72]1[S:71][N:70]=[C:69](/[C:57](=[N:58]/[OH:59])/[C:56]([NH:16][C@@H:13]2[C:12](=[O:25])[N:11]3[C@@H:14]2[S:15][CH2:8][C:9](/[CH:29]=[C:30]2/[C:31](=[O:47])[N:32]([C@@H:35]4[CH2:39][CH2:38][NH:37][CH2:36]4)[CH2:33][CH2:34]/2)=[C:10]3[C:26]([OH:28])=[O:27])=[O:55])[N:73]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 90407255HCID 90407255, compoundHCID 178489948HCID 178489948, compound

Product 1

HCID 135413542Ceftobiprole

Reagents, catalysts & solvents 1

HCID 15413
tert-Butyl methyl ether
Solvent

Procedure

A reactor is charged with (7R)-4-methoxybenzyl-3-((E)-((R)-1′-(tert-butoxycarbonyl)-2-oxo-[1,3′-bipyrrolidin]-3-ylidene)methyl)-7-((Z)-(2-hydroxybenzylidene)amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (1 eq), water (6-9 weight % relative to the Schiff base), (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(((4-methoxybenzyl)oxy)imino)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-78c1381f904e41eb81fa106c2d13ae1e
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006421B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes