Iodoacetamide → HCID 10281490, compound

HRID 1072376Notes

Reaction equation

[OH:1][C@@H:2]([C@H:4]1[C:46](=[O:47])[N:6]2[C:7]([C:33]([O:35]CC3C=CC([N+]([O-])=O)=CC=3)=[O:34])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[C:25]([C:27]6[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=6)[CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].I[CH2:49][C:50]([NH2:52])=[O:51]>>[C:50]([CH2:49][N+:23]1[CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:26]=[C:21]([C:19]([C:16]2[N:17]=[CH:18][N:13]3[CH:12]=[C:11]([C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:46](=[O:47])[N:6]5[C:7]=4[C:33]([O-:35])=[O:34])[S:15][C:14]=23)=[O:20])[CH:22]=1)(=[O:51])[NH2:52]

Participants

Reactant 2

HCID 3727Iodoacetamide

HCID 91269457HCID 91269457, compound

Product 1

HCID 10281490HCID 10281490, compoundYield 19.6%

Procedure

An N-quaternarized compound (91 mg) was prepared in substantially the same manner as in Example 24, except that 97 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(5-phenylpyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate and 185 mg of 2-iodoacetamide were used as the starting compounds. The title compound (16.7 mg) was prepared in substantially the same manner as in step c) of Example 1, except that this compound was used as the starting compound.

Sources & evidence

ORD record: ord-6d6b88d61fbf454da547f73e31df2f59
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908913B2

Reaction notes

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