Iodoacetamide → HCID 131727434, compound

HRID 230046Notes

Reaction equation

[I:1][CH2:2][C:3]([NH2:5])=[O:4].[OH:6][C@@H:7]([C@H:9]1[C:38](=[O:39])[N:11]2[C:12]([C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])=[C:13]([C:16]3[S:20][C:19]4=[C:21]([C:24]([C:26]5[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=5)=[O:25])[N:22]=[CH:23][N:18]4[CH:17]=3)[C@H:14]([CH3:15])[C@H:10]12)[CH3:8].C(OCC)(=O)C>CO>[I-:1].[C:3]([CH2:2][N+:28]1[CH:29]=[CH:30][CH:31]=[C:26]([C:24]([C:21]2[N:22]=[CH:23][N:18]3[CH:17]=[C:16]([C:13]4[C@H:14]([CH3:15])[C@@H:10]5[C@@H:9]([C@H:7]([OH:6])[CH3:8])[C:38](=[O:39])[N:11]5[C:12]=4[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])[S:20][C:19]=23)=[O:25])[CH:27]=1)(=[O:4])[NH2:5]

Participants

Conditions

Temperature: 40 °C

Procedure

2-Iodoacetamide (1.13 g) was added to a solution of 1.46 g of allyl (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonyl-imidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate in 4.5 ml of methanol, and the mixture was stirred at 40° C. for 22 hr. Methanol (8 ml) was added thereto for dilution. The diluted reaction mixture was added dropwise to 180 ml of ethyl acetate, and the resultant powder was collected by filtration to give 1.80 g of allyl (1S,5R,6S)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate iodide.

Workup

customThe diluted reaction mixture
filtrationthe resultant powder was collected by filtration

Sources & evidence

ORD record: ord-6ea611df0cc24203b474607bba39f550
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563901B2

Reaction notes

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