Diphenylphosphinic chloride → BocPro-Phe-PheOMe

HRID 2418583Notes

Reaction equation

[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[NH2:16][C@H:17]([C:26]([NH:28][C@H:29]([C:37]([O:39][CH3:40])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22]C=1.Cl.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1>>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:16][C@H:17]([C:26]([NH:28][C@H:29]([C:37]([O:39][CH3:40])=[O:38])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:27])[CH2:18][C:19]1[CH:20]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:5]

Participants

Reactant 3

HCID 73910Diphenylphosphinic chloride

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

HCID 131713766HCID 131713766, compound

Product 1

HCID 131713692BocPro-Phe-PheOMeYield 67%

Procedure

Condensation of ZPheOH (29.2 g.) and HPheOMe (21.6 g.) by the mixed anhydride method using isobutyl chloroformate gave ZPhe-PHeOMe in 57% yield. Debenzyloxycarbonylation of ZPhe-PHeOMe (26.4 g.) by hydrogenation in acidified methanol with palladium catalyst gave HPhe-PheOMe in 86% yield. Condensation of BocProOH (6.46 g.) and HPhe-PheOMe hydrochloride (10.9 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-Phe-PheOMe in 67% yield. Hydrazinolysis of BocPro-Phe-PheOMe (9.57 g.) gave BocPro-Phe-Phe-NHNH2 in 92% yield.

Sources & evidence

ORD record: ord-6ddaf885ad7a4247ab024bb8e621605e
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

Loading…