Diphenylphosphinic chloride → HCID 131713776, compound

HRID 2418591Notes

Reaction equation

HRID 2418591 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][C@H:21]([C:27]([O:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31])=[O:28])[CH2:22][CH2:23][CH:24](C)C.Br.[C:39]1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1>>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([NH:20][C@H:21]([C:27]([O:29][C:30]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:31])=[O:28])[CH2:22][CH:23]([CH3:24])[CH3:39])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 637610Boc-D-phenylalanineHCID 131713777HCID 131713777, compound

Product 1

HCID 131713776HCID 131713776, compoundYield 54%

Procedure

Condensation of BocDPheOH (2.65 g.) and HLeuOBz hydrobromide salt (3.02 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocDPhe-LeuOBz in 54% yield. Debenzylation of BocDPhe-LeuOBz (2.25 g.) by hydrogenation with palladium catalyst gave BocDPhe-LeuOH in 87% yield. Condensation of BocDPhe-LeuOH (1.50 g.) and HNleNH2 hydrochloride salt (0.667 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocDPhe-Leu-NleNH2 in 60% yield. De-t-butoxycarbonylation of BocDPhe-Leu-NleNH2 (1.00 g.) using hydrogen chloride in acetic acid gave HDPhe-Leu-NleNH2 hydrochloride salt in 79% yield.

Sources & evidence

ORD record
ord-fb5b6b00397042b9847e7bc3d42fcf0c
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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