Phenylmethanesulfonyl chloride → (S)-Methyl 3-methyl-2-(1-oxo-6-(4-(phenylmethylsulfonamido)phenyl)isoindolin-2-yl)butanoate

HRID 403768Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][N:13]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[C:14]3=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:26]([S:33](Cl)(=[O:35])=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH3:24][CH:23]([CH3:25])[C@H:18]([N:13]1[CH2:12][C:11]2[C:15](=[CH:16][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:33]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:35])=[O:34])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[C:14]1=[O:17])[C:19]([O:21][CH3:22])=[O:20]

Participants

Reactant 2

HCID 74740Phenylmethanesulfonyl chloride

HCID 131731441(S)-Methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731464(S)-Methyl 3-methyl-2-(1-oxo-6-(4-(phenylmethylsulfonamido)phenyl)isoindolin-2-yl)butanoate

Procedure

The compound of example 93 was prepared analogous to compound of example 77 by reaction of compound of example 6 with benzyl sulfonyl chloride. The compound of example 93 was used directly without isolation for the preparation of compound of example 94.

Sources & evidence

ORD record: ord-109baa65a59d4d9a86854728922ef327
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748426B2

Reaction notes

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