Iodoacetamide → HCID 178462283, compound

HRID 1088638Notes

Reaction equation

HRID 1088638 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:50])[C:7]([S:25][C@@H:26]1[CH2:30][N:29]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=3)=[O:32])[C@H:28]([CH2:44][N:45]3[CH:49]=[CH:48][N:47]=[CH:46]3)[CH2:27]1)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13])[CH3:3].[I:51][CH2:52][C:53]([NH2:55])=[O:54]>C(#N)C>[I-:51].[C:53]([CH2:52][N:47]1[CH:48]=[CH:49][N+:45]([CH2:44][C@@H:28]2[CH2:27][C@H:26]([S:25][C:7]3[C@H:6]([CH3:50])[C@H:5]4[N:9]([C:10](=[O:11])[C@@H:4]4[C@H:2]([OH:1])[CH3:3])[C:8]=3[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[CH2:30][N:29]2[C:31]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=2)=[O:32])=[CH:46]1)(=[O:54])[NH2:55]

Participants

4

Reactant 2

HCID 3727IodoacetamideHCID 15086182HCID 15086182, compound

Product 1

HCID 178462283HCID 178462283, compoundYield 142.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2S,4S)-2-(imidazol-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.80 g) and iodoacetamide (0.62 g) in acetonitrile (16 ml) was stirred at ambient temperature for 60 hours. The mixture was concentrated under reduced pressure to give crude 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(3-carbamoylmethyl-1-imidazolio)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (1.44 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f9e1129a638d49baadb7247ccf6418c3
Source dataset
uspto-grants-1990_10
Patent number
US04963544

Reaction notes

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