4-Chlorobenzenesulfonyl chloride → HCID 23385658, compound

HRID 1282509Notes

Reaction equation

HRID 1282509 reaction equation
C(OC([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.FC(F)(F)C([O-])=O.[Cl:51][C:52]1[CH:57]=[CH:56][C:55]([S:58](Cl)(=[O:60])=[O:59])=[CH:54][CH:53]=1>>[Cl:51][C:52]1[CH:57]=[CH:56][C:55]([S:58]([NH:8][C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][CH:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]3[C:30]2=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:15])(=[O:60])=[O:59])=[CH:54][CH:53]=1

Participants

5

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 84468TrifluoroacetateHCID 16211325N~2~-(tert-Butoxycarbonyl)-N~5~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-ornithineHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 23385658HCID 23385658, compoundYield 33%

Procedure

Nα-tert-butoxycarbonyl-Nδ-(9-fluorenylmethoxycarbonyl)-L-ornithine 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 33% yield.

Sources & evidence

ORD record
ord-8c426ea17f4d4ba88685213ce7763f5f
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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