3-(Boc-amino)-L-alanine → ZPhe-LDap(Boc)OH

HRID 2418567Notes

Reaction equation

HRID 2418567 reaction equation
[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:2]([C:10]([O:12]N1C(=O)CCC1=O)=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:30][C@H:31]([C:41]([OH:43])=[O:42])[CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>>[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[C@H:2]([C:10]([NH:30][C@H:31]([C:41]([OH:43])=[O:42])[CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:35])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 103528593-(Boc-amino)-L-alanineHCID 12876457N-Carbobenzyloxy-L-phenylalanyl N-hydroxysuccinimide ester

Product 1

HCID 131713742ZPhe-LDap(Boc)OHYield 64%

Procedure

Condensation of ZPheOSu (6.96 g.) and HLDap(Boc)OH (6.0 g.) by the salt coupling method gave ZPhe-LDap(Boc)OH in 64% yield. Condensation of ZPhe-LDap(Boc)OH (4.85 g.) and HLeuOMe (2.73 g.) by the mixed anhydride method using diphenylphosphinic chloride gave ZPhe-LDap(Boc)-LeuOMe in 69% yield. Debenzyloxycarbonylation of ZPhe-LDap(Boc)-LeuOMe (4.15 g.) by hydrogenation with palladium catalyst gave HPhe-LDap(Boc)-LeuOMe in 100% yield. Condensation of BocPro-PheOH (1.09 g.) and HPhe-LDap(Boc)-LeuOMe (1.44 g.) using dicyclohexylcarbodiimide and N-hydroxynorbornenedicarboximide gave BocPro-Phe-Phe-LDap(Boc)-LeuOMe in 75% yield. Hydrazinolysis of BocPro-Phe-Phe-LDap(Boc)-LeuOMe (1.69 g.) gave BocPro-Phe-Phe-LDap(Boc)- LeuNHNH2 in 36% yield.

Sources & evidence

ORD record
ord-076e0beeab714d83b37ab1d58fb33cc2
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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