Iodoacetamide →

HRID 975718Notes

Reaction equation

HRID 975718 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][C:33]1[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=1)=[O:6])[CH:2]=[CH2:3].[I:39][CH2:40][C:41]([NH2:43])=[O:42]>CC(C)=O>[I-:39].[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][CH2+:33]1[N:37]([CH2:40][C:41](=[O:42])[NH2:43])[CH:36]=[CH:35][N:34]1[CH3:38])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 3727IodoacetamideHCID 57288318HCID 57288318, compound

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(1-methylimidazol-2-yl)ethyl}-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.04 g) in acetone (5 ml) was added iodoacetamide (1.06 g) with stirring at ambient temperature and then allowed to stand overnight. The reaction mixture was evaporated in vacuo and dried in vacuo for 1 hour to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(3-carbamoylmethyl-1-methyl-2-imidazolio) ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (1.39 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customdried in vacuo for 1 hour

Sources & evidence

ORD record
ord-0de561248c9342d99c9bea754d28010d
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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