2,2,2-Trifluoroethanesulfonyl 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 2,2,2-trifluoroethanesulfonate

HRID 628134Notes

Reaction equation

[F:1][C:2]([F:9])([F:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].[OH:10][C@:11]([CH3:47])([CH2:45][OH:46])[C:12](=[O:44])[C@@H:13]([NH:21][C:22](=[O:43])[C@@H:23]([NH:27][C:28](=[O:42])[C@@H:29]([NH:33][C:34]([C:36]1[S:40][C:39]([CH3:41])=[N:38][CH:37]=1)=[O:35])[CH2:30][O:31][CH3:32])[CH2:24][O:25][CH3:26])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[F:1][C:2]([F:9])([F:8])[CH2:3][S:4]([O:46][CH2:45][C@:11]([OH:10])([CH3:47])[C:12](=[O:44])[C@@H:13]([NH:21][C:22](=[O:43])[C@@H:23]([NH:27][C:28](=[O:42])[C@@H:29]([NH:33][C:34]([C:36]1[S:40][C:39]([CH3:41])=[N:38][CH:37]=1)=[O:35])[CH2:30][O:31][CH3:32])[CH2:24][O:25][CH3:26])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:6])=[O:5]

Participants

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl 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 72737702(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 2,2,2-trifluoroethanesulfonate

Procedure

Prepared according to procedures described above, by reacting 2,2,2-trifluoroethanesulfonyl 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 C27H35F3N4O10S2 m/z: 697 (M+H)+.

Workup

customPrepared

Sources & evidence

ORD record: ord-c7e1c59b13a84ca9a4eb0009ff1cbd94
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309283B2

Reaction notes

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