4-Chlorobenzenesulfonyl chloride → Nalpha-(4-Chlorobenzenesulfonyl)-Nepsilon-(9-fluorenylmethoxycarbonyl)-L-lysine

HRID 1282508Notes

Reaction equation

HRID 1282508 reaction equation
C(OC([NH:8][C@H:9]([C:32]([OH:34])=[O:33])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.FC(F)(F)C([O-])=O.[Cl:52][C:53]1[CH:58]=[CH:57][C:56]([S:59](Cl)(=[O:61])=[O:60])=[CH:55][CH:54]=1>>[Cl:52][C:53]1[CH:58]=[CH:57][C:56]([S:59]([NH:8][C@H:9]([C:32]([OH:34])=[O:33])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][CH:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:16])(=[O:61])=[O:60])=[CH:55][CH:54]=1

Participants

5

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 84468TrifluoroacetateHCID 10983524(2S)-2-(((tert-butoxy)carbonyl)amino)-6-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acidHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 86604340Nalpha-(4-Chlorobenzenesulfonyl)-Nepsilon-(9-fluorenylmethoxycarbonyl)-L-lysineYield 38%

Procedure

Nα-tert-butoxycarbonyl-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine was deprotected at the α position by treatment with TFA/CH2Cl2 as described in the procedure outlined in example 24 and the resulting trifluoroacetate salt was alkylated with 4-chlorobenzenesulfonyl chloride as described in example 2, affording the title compound in 38% yield.

Sources & evidence

ORD record
ord-f7a5acf4154c40a4bf2ded61cdc06645
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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