Methyl iodide → HCID 86628547, compound

HRID 732680Notes

Reaction equation

HRID 732680 reaction equation
[N:1]1([C:6]([N:8]2[CH2:12][C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@@H:10]([CH2:19][N:20]([C@@H:28]([C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[CH3:29])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:9]2)=[O:7])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:40][I:41]>C(#N)C>[I-:41].[C:23]([O:22][C:21]([N:20]([CH2:19][C@@H:10]1[C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][N:8]([C:6]([N:1]2[CH:5]=[CH:4][N+:3]([CH3:40])=[CH:2]2)=[O:7])[CH2:9]1)[C@@H:28]([C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)[CH3:29])=[O:27])([CH3:25])([CH3:24])[CH3:26]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86628546HCID 86628546, compound

Product 1

HCID 86628547HCID 86628547, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 40 ml acetonitrile solution of 1.234 g of tert-butyl {[(3R,4S)-1-(1H-imidazol-1-ylcarbonyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate was mixed with 0.60 ml of methyl iodide and stirred overnight at room temperature. By evaporating the reaction solution under a reduced pressure, 1.966 g of 1-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}-3-methyl-1H-imidazol-3-ium iodide was obtained as a pale yellow solid . . . EP: 539.

Workup

  1. customBy evaporating the reaction solution under a reduced pressure

Sources & evidence

ORD record
ord-680caff8c9054c0cb45e4cb353db3a5f
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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