Methyl iodide → (R)-4-(benzyloxy)-N,N,N-trimethyl-4-oxo-2-(6-phenoxypyridine-3-sulfonamido)butan-1-aminium iodide

HRID 1958718Notes

Reaction equation

HRID 1958718 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][C@H:4]([NH:16][S:17]([C:20]1[CH:21]=[N:22][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH3:34][I:35]>C(Cl)Cl>[I-:35].[CH2:9]([O:8][C:6](=[O:7])[CH2:5][C@@H:4]([NH:16][S:17]([C:20]1[CH:21]=[N:22][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH2:3][N+:2]([CH3:34])([CH3:1])[CH3:33])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86641216(R)-benzyl 4-(dimethylamino)-3-(6-phenoxypyridine-3-sulfonamido)butanoate

Product 1

HCID 68742884(R)-4-(benzyloxy)-N,N,N-trimethyl-4-oxo-2-(6-phenoxypyridine-3-sulfonamido)butan-1-aminium iodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-benzyl 4-(dimethylamino)-3-(6-phenoxypyridine-3-sulfonamido)butanoate in CH2Cl2 (2 mL) was added methyl iodide (100 pit). The reaction was stirred overnight and concentrated to dryness to give the title compound in quantitative yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.63 (s, 1H), 8.26 (d, J=8.8 Hz, 1H), 7.43 (t, J=7.7 Hz, 2H), 7.39-7.29 (m, 5H), 7.13 (d, J=8.1 Hz, 2H), 6.99 (d, 1H, J=8.8 Hz, 1H) 5.14-5.03 (m, 2H), 4.49-4.41 (m, 1H), 4.36-4.30 (m, 1H), 3.74-3.71 (m, 1H), 3.42 (s, 9H), 2.91-2.84 (m, 1H), 2.46-2.42 (m, 1H).

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ccabe881a5464c4a83200492ddf804ef
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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