Iodoacetamide → HCID 20612195, compound

HRID 1840466Notes

Reaction equation

[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28]CC3C=CC([N+]([O-])=O)=CC=3)=[O:27])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=5)[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].I[CH2:42][C:43]([NH2:45])=[O:44].C(OCC)(=O)C>CC(C)=O>[C:43]([CH2:42][N+:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:19][C:16]1[N:17]=[CH:18][N:13]2[CH:12]=[C:11]([C:8]3[C@H:9]([CH3:10])[C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:39](=[O:40])[N:6]4[C:7]=3[C:26]([O-:28])=[O:27])[S:15][C:14]=12)(=[O:44])[NH2:45]

Participants

Conditions

Temperature: 40 °C

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-2-yl)thioimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (42.2 mg) was dissolved in 2 ml of acetone. 2-Iodoacetamide (140 mg) was added to the solution. The mixture was stirred at 40° C. for 4 days. Ethyl acetate (4 ml) was added to the reaction solution, and the resultant precipitate was collected, and was reacted in the same manner as in Example 1c). The reaction product was purified by column chromatography on Cosmosil 40C18-PREP (a 10 to 25% aqueous methanol solution). In this case, the first eluted fraction in two major products was collected to prepare 1.44 mg of the title compound.

Workup

customthe resultant precipitate was collected
customwas reacted in the same manner as in Example 1c)
customThe reaction product was purified by column chromatography on Cosmosil 40C18-PREP (a 10 to 25% aqueous methanol solution)
customIn this case, the first eluted fraction in two major products was collected
customto prepare 1.44 mg of the title compound

Sources & evidence

ORD record: ord-9af12028171c4f83a022c6259cb99928
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680313B2

Reaction notes

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