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

HRID 1282507Notes

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.[N+:52]([C:55]1[CH:60]=[CH:59][C:58]([S:61](Cl)(=[O:63])=[O:62])=[CH:57][CH:56]=1)([O-:54])=[O:53]>>[N+:52]([C:55]1[CH:60]=[CH:59][C:58]([S:61]([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:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])(=[O:63])=[O:62])=[CH:57][CH:56]=1)([O-:54])=[O:53]

Participants

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chloride

HCID 84468Trifluoroacetate

HCID 10983524(2S)-2-(((tert-butoxy)carbonyl)amino)-6-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

HCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 86604339Nalpha-(4-nitrobenzenesulfonyl)-Nepsilon-(9-fluorenylmethoxycarbonyl)-L-lysineYield 51%

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-nitrobenzenesulfonyl chloride as described in example 2, affording the title compound in 51% yield.

Sources & evidence

ORD record: ord-127337dbb0f04e9d92ef78c7faff48c7
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455587B1

Reaction notes

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