Diethyl Ether → HCID 69364166, compound

HRID 1072374Notes

Reaction equation

HRID 1072374 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:44](=[O:45])[N:6]2[C:7]([C:31]([O:33]CC3C=CC([N+]([O-])=O)=CC=3)=[O:32])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][C:24]6[C:29]([CH:30]=5)=[CH:28][CH:27]=[CH:26][CH:25]=6)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].CI.[CH2:48](OCC)C>C(#N)C.C(Cl)(Cl)Cl>[OH:1][C@@H:2]([C@H:4]1[C:44](=[O:45])[N:6]2[C:7]([C:31]([O-:33])=[O:32])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N+:23]([CH3:48])[C:28]6[C:29]([CH:30]=5)=[CH:24][CH:25]=[CH:26][CH:27]=6)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 91285261HCID 91285261, compound

Product 1

HCID 69364166HCID 69364166, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(quinolin-3-yl)carbonylimidazo[5,1-b]-thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (93 mg) was dissolved in acetonitrile (2.25 ml)/chloroform (0.75 ml) to prepare a solution. Methyl iodide (0.063 ml) was added to the solution at room temperature, and the mixture was stirred at 40° C. for 3 days. The reaction solution was poured into diethyl ether to produce a powder which was filtered to give an N-quaternarized compound. The title compound (7.7 mg) was prepared in substantially the same manner as in step b) of Example 1, except that this compound was used as the starting compound.

Workup

  1. customto prepare a solution
  2. customto produce a powder which
  3. filtrationwas filtered
  4. customto give an N-quaternarized compound

Sources & evidence

ORD record
ord-e8437ca43e454e43bb22bc278b55e3f9
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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