Diphenylphosphinic chloride → HCID 131713734, compound

HRID 2418563Notes

Reaction equation

HRID 2418563 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]([N:28]([CH3:41])[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.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]([N:28]([CH3:41])[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

4

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 131713735HCID 131713735, compound

Product 1

HCID 131713734HCID 131713734, compoundYield 73%

Procedure

Condensation of BocPheOPFP (8.63 g.) and MePHeOMe (5.50 g.) by the active ester method gave BocPhe-MePheOMe in 95% yield. De-t-butoxycarbonylation of BocPhe-MePheOMe using hydrogen chloride in ethyl acetate gave HPhe-MePHeOMe in 48% yield. Condensation of BocProOH (0.71 g.) and HPhe-MePheOMe (1.13 g.) by the mixed anhydride method using diphenylphosphinic chloride gave BocPro-Phe-MePheOMe in 73% yield. Hydrazinolysis of BocPro-Phe-MePheOMe (3.10 g.) gave BocPro-Phe-MePheNHNH2 in 84% yield.

Sources & evidence

ORD record
ord-244299fd3b624040a6d4e7b96aa51aa2
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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