Hydrochloric Acid → HPro-Phe-Phe-LDap-Leu-MetNH2

HRID 2418569Notes

Reaction equation

HRID 2418569 reaction equation
[N:1]1([C:60](OC(C)(C)C)=O)[CH2:59][CH2:58][CH2:57][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:38]([NH:40][C@H:41]([C:46]([NH:48][C@H:49]([C:54]([NH2:56])=[O:55])[CH2:50][CH2:51][S:52][CH3:53])=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:29][NH:30]C(OC(C)(C)C)=O)=[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].Cl>C(O)(=O)C>[NH:1]1[CH2:60][CH2:59][CH2:58][CH2:57][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:38]([NH:40][C@H:41]([C:46]([NH:48][C@H:49]([C:54]([NH2:56])=[O:55])[CH2:50][CH2:51][S:52][CH3:53])=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:29][NH2:30])=[O:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713745HCID 131713745, compound

Product 1

HCID 131713744HPro-Phe-Phe-LDap-Leu-MetNH2

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocPro-Phe-Phe-LDap(Boc)-LeuNHNH2 (607 mg.) and HMetNH2 (150 mg.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-Phe-Phe-LDap(Boc)-Leu-MetNH2 in 67% yield. De-t-butoxycarbonylation of BocPro-Phe-Phe-LDap(Boc)-Leu-MetNH2 (430 mg.) using hydrogen chloride in acetic acid gave HPro-Phe-Phe-LDap-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:2) salt dihydrate in 95% yield.

Sources & evidence

ORD record
ord-48874befaa694071ae07f58fbc35ddd4
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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