Methanesulfonyl chloride → (2R,4S)-2-Hydroxy-4-((S)-3-methoxy-2-((S)-3-methoxy-2-(2-methylthiazole-5-carboxamido)propanamido)propanamido)-2-methyl-3-oxo-5-phenylpentyl methanesulfonate

HRID 628133Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@:7]([CH3:43])([CH2:41][OH:42])[C:8](=[O:40])[C@@H:9]([NH:17][C:18](=[O:39])[C@@H:19]([NH:23][C:24](=[O:38])[C@@H:25]([NH:29][C:30]([C:32]1[S:36][C:35]([CH3:37])=[N:34][CH:33]=1)=[O:31])[CH2:26][O:27][CH3:28])[CH2:20][O:21][CH3:22])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:1][S:2]([O:42][CH2:41][C@:7]([OH:6])([CH3:43])[C:8](=[O:40])[C@@H:9]([NH:17][C:18](=[O:39])[C@@H:19]([NH:23][C:24](=[O:38])[C@@H:25]([NH:29][C:30]([C:32]1[S:36][C:35]([CH3:37])=[N:34][CH:33]=1)=[O:31])[CH2:26][O:27][CH3:28])[CH2:20][O:21][CH3:22])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:4])=[O:3]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 86715357N-((S)-1-(((S)-1-(((2S,4R)-4,5-dihydroxy-4-methyl-3-oxo-1-phenylpentan-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)-2-methylthiazole-5-carboxamide

Product 1

HCID 72737659(2R,4S)-2-Hydroxy-4-((S)-3-methoxy-2-((S)-3-methoxy-2-(2-methylthiazole-5-carboxamido)propanamido)propanamido)-2-methyl-3-oxo-5-phenylpentyl methanesulfonate

Procedure

Prepared according to procedures described above, by reacting methanesulfonyl chloride with N—((S)-1-(((S)-1-(((2S,4R)-4,5-dihydroxy-4-methyl-3-oxo-1-phenylpentan-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)amino)-3-methoxy-1-oxopropan-2-yl)-2-methylthiazole-5-carboxamide. MS for C26H36N4O10S2 m/z: 629 (M+H)+.

Workup

customPrepared

Sources & evidence

ORD record: ord-166eb94aee304cf7a73fc49051ccc881
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309283B2

Reaction notes

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