Iodoacetamide → HCID 15056108, compound

HRID 1590512Notes

Reaction equation

HRID 1590512 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[CH2:49][CH2:48][CH2:47][CH2:46]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]>CC(C)=O>[I-:51].[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:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=3)=[O:32])[C@H:28]([CH2:44][N+:45]3([CH2:52][C:53](=[O:54])[NH2:55])[CH2:49][CH2:48][CH2:47][CH2:46]3)[CH2:27]1)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)=[O:13])[CH3:3]

Participants

4

Reactant 2

HCID 3727IodoacetamideHCID 15056072HCID 15056072, compound

Product 1

HCID 15056108HCID 15056108, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(pyrrolidin-1-yl)methylpyrrolidin-4-yl]thio-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.77 g) in acetone (8 ml) was added iodoacetamide (0.93 g) at ambient temperature. The mixture was stirred overnight at the same temperature. The reaction mixture was evaporated in vacuo to give 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2S,4S)-2-(1-carbamoylmethylpyrrolidinio)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (0.71 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-76333d7a44604757b3203c3918e8af28
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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