Methyl iodide → methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoyl-amino)propanoate

HRID 517506Notes

Reaction equation

[C:1](=O)([O-])[O-].[K+].[K+].CI.[OH:9][C:10]1[CH:34]=[CH:33][C:13]([C:14]([NH:16][CH2:17][C@H:18]([N:23]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]2)[C:19]([O:21][CH3:22])=[O:20])=[O:15])=[CH:12][CH:11]=1>C(C(C)=O)C>[CH3:32][S:29]([N:26]1[CH2:25][CH2:24][N:23]([C@@H:18]([CH2:17][NH:16][C:14](=[O:15])[C:13]2[CH:33]=[CH:34][C:10]([O:9][CH3:1])=[CH:11][CH:12]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:28][CH2:27]1)(=[O:31])=[O:30]

Participants

Conditions

Temperature: 80 °C

Procedure

100 mg (0.8 mmol) of potassium carbonate and 0.1 ml (2 mmol) of methyl iodide are added to a solution of 250 mg (0.7 mmol) of methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate in 10 ml of methyl ethyl ketone. The reaction medium is heated at 80° C. for 4 h. After cooling, it is filtered then concentrated. 260 mg (100%) of methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-(4-methoxybenzoylamino)-propanoate are obtained in the form of a white solid.

Workup

temperatureAfter cooling
filtrationit is filtered
concentrationthen concentrated

Sources & evidence

ORD record: ord-080bb2b697164526b0217cdf7c60fa1f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115102B2

Reaction notes

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