2,2-Difluoroethanesulfonyl 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-difluoroethanesulfonate

HRID 628136Notes

Reaction equation

HRID 628136 reaction equation
[F:1][CH:2]([F:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].[OH:9][C@:10]([CH3:46])([CH2:44][OH:45])[C:11](=[O:43])[C@@H:12]([NH:20][C:21](=[O:42])[C@@H:22]([NH:26][C:27](=[O:41])[C@@H:28]([NH:32][C:33]([C:35]1[S:39][C:38]([CH3:40])=[N:37][CH:36]=1)=[O:34])[CH2:29][O:30][CH3:31])[CH2:23][O:24][CH3:25])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[F:1][CH:2]([F:8])[CH2:3][S:4]([O:45][CH2:44][C@:10]([OH:9])([CH3:46])[C:11](=[O:43])[C@@H:12]([NH:20][C:21](=[O:42])[C@@H:22]([NH:26][C:27](=[O:41])[C@@H:28]([NH:32][C:33]([C:35]1[S:39][C:38]([CH3:40])=[N:37][CH:36]=1)=[O:34])[CH2:29][O:30][CH3:31])[CH2:23][O:24][CH3:25])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:6])=[O:5]

Participants

3

Reactant 2

HCID 509894052,2-Difluoroethanesulfonyl chlorideHCID 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 72737704(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-difluoroethanesulfonate

Procedure

Prepared according to procedures described above, by reacting 2,2-difluoroethanesulfonyl 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 C27H36F2N4O10S2 m/z: 679 (M+H)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f3ed7bbf7f324abc92d1cbe58f0e8612
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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