4-Toluenesulfonyl chloride → (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(p-tolylsulfonylamino)hexanoic acid

HRID 1282488Notes

Reaction equation

HRID 1282488 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:25]([OH:27])=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>>[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]([C:25]([OH:27])=[O:26])[NH:18][C:16]([O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[O:17])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 7010557(2S)-6-amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid

Product 1

HCID 3013737(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(p-tolylsulfonylamino)hexanoic acidYield 71%

Procedure

Nα-(9-fluorenylmethoxycarbonyl)-L-lysine was reacted with 4-methylbenzenesulfonyl chloride under the conditions used in example 2 giving 71% of the title compound.

Sources & evidence

ORD record
ord-b12d6befcdad4cfc80d9628d221a98a3
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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