D-Phenylalanine → BocPro-DPheOH

HRID 2418557Notes

Reaction equation

HRID 2418557 reaction equation
[N:1]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5]N1C(=O)CCC1=O)=O.[NH2:23][C@@H:24]([C:32]([OH:34])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[N:1]1([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([NH:23][C@@H:24]([C:32]([OH:34])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5]

Participants

3

Reactant 2

HCID 71567D-PhenylalanineHCID 8538831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) 2-(2,5-dioxo-1-pyrrolidinyl) ester, (2S)-

Product 1

HCID 7019894BocPro-DPheOHYield 67%

Procedure

Condesation of BocProOH (6.46 g.) and N-hydroxysuccinimide (3.5 g.) using dicyclohexylcarbodiimide gave BocProOSu in 75% yield. Condensation of BocProOSu (5.0 g.) and HDPheOH (2.75 g.) by the salt coupling method gave BocPro-DPheOH in 67% yield. Condensation of BocPro-DPheOH (3.98 g.) and HPheOMe hydrochloride salt (2.4 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-DPhe-PheOMe in 74% yield. Hydrazinolysis of Boc-Pro-DPhe-PheOMe (3.14 g.) gave BocPro-DPhe-PheNHNH2 in 79% yield.

Sources & evidence

ORD record
ord-3c8bd2ac24d84b7daf40ec0f581d2598
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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