BocPro-DPhe-PheNHNH2 → BocPro-DPhe-Phe-DPhe-Leu-MetNH2

HRID 2418587Notes

Reaction equation

HRID 2418587 reaction equation
[N:1]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][CH2:29][C@H:2]1[C:3]([NH:5][C@@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27]N)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].N[C@@H:40]([C:48]([NH:50][C@H:51]([C:56]([NH:58][C@H:59]([C:64]([NH2:66])=[O:65])[CH2:60][CH2:61][S:62][CH3:63])=[O:57])[CH2:52][CH:53]([CH3:55])[CH3:54])=[O:49])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl>>[N:1]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][CH2:29][C@H:2]1[C:3]([NH:5][C@@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@@H:40]([C:48]([NH:50][C@H:51]([C:56]([NH:58][C@H:59]([C:64]([NH2:66])=[O:65])[CH2:60][CH2:61][S:62][CH3:63])=[O:57])[CH2:52][CH:53]([CH3:54])[CH3:55])=[O:49])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 131713729BocPro-DPhe-PheNHNH2HCID 131713768HDPhe-Leu-MetNH2 hydrochloride

Product 1

HCID 131713770BocPro-DPhe-Phe-DPhe-Leu-MetNH2Yield 91%

Procedure

Condensation of BocPro-DPhe-PheNHNH2 (2.09 g.) and HDPhe-Leu-MetNH2 hydrochloride salt (1.78 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-DPhe-Phe-DPhe-Leu-MetNH2 in 91% yield. De-t-butoxycarbonylation of BocPro-DPhe-Phe-DPhe-Leu-MetNH2 (2.32 g.) using hydrogen chloride in ethyl acetate gave HPro-DPhe-Phe-DPhe-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt dihydrate in 44% yield.

Sources & evidence

ORD record
ord-2c061801ee6d4c23be4bcc4d0dc1cd9e
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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