Methyl iodide → HCID 88466713, compound

HRID 1586752Notes

Reaction equation

HRID 1586752 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]([CH3:54])[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[CH2:50][CH2:49][CH2:48][N:47]4[N:51]=[CH:52][CH:53]=[C:46]34)[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].[CH3:55][I:56]>CC(C)=O.O1CCCC1>[I-:56].[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:54])[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][NH+:45]3[CH2:50][CH2:49][CH2:48][N:47]4[N:51]([CH3:55])[CH2:52][CH:53]=[C:46]34)[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]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 57089100HCID 57089100, compound

Product 1

HCID 88466713HCID 88466713, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl) -2-{4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-4yl}methylpyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate (0.78 g) in a mixture of acetone (8 ml) and tetrahydrofuran (16 ml) was added methyl iodide (0.64 ml) with stirring and the mixture was allowed to stand at ambient temperature overnight. The reaction mixture was evaporated in vacuo to give 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitro benzyloxycarbonyl)-2-{1-methyl-4,5,6,7-tetrahydro-4-pyrazolo [1,5-a]primidinio}methylpyrrolidin-4yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (0.88 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-f4f00910e5c441d199afa5b3c4df874e
Source dataset
uspto-grants-1993_06
Patent number
US05215983

Reaction notes

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