Diphenylphosphinic chloride → ZPhe-LDap(Boc)-LeuOMe

HRID 2418568Notes

Reaction equation

[NH:1]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C@H:2]([C:10]([NH:12][C@H:13]([C:23](O)=[O:24])[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:36][C@H:37]([C:43]([O:45][CH3:46])=[O:44])[CH2:38][CH2:39][CH:40](C)C.[C:47]1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1>>[NH:1]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C@H:2]([C:10]([NH:12][C@H:13]([C:23]([NH:36][C@H:37]([C:43]([O:45][CH3:46])=[O:44])[CH2:38][CH:39]([CH3:40])[CH3:47])=[O:24])[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 73910Diphenylphosphinic chloride

HCID 22859486Methyl (2S)-2-amino-5-methylhexanoate

HCID 131713742ZPhe-LDap(Boc)OH

Product 1

HCID 131713743ZPhe-LDap(Boc)-LeuOMeYield 69%

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-51489d359415475480012eb70530f961
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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