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

HRID 2418571Notes

Reaction equation

HRID 2418571 reaction equation
[N:1]1([C:45](OC(C)(C)C)=O)[CH2:44][CH2:43][CH2:42][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](NN)=[O:39])[CH2:29][CH2:30][C:31](=[O:37])[O:32]C(C)(C)C)=[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].[NH2:52][C@H:53]([C:59]([NH:61][C@H:62]([C:67]([NH2:69])=[O:68])[CH2:63][CH2:64][S:65][CH3:66])=[O:60])[CH2:54][CH2:55][CH:56](C)C.Cl.N1(C(OC(C)(C)C)=O)CCC[C@H:72]1C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N)=O)CCSC)=O)CC(C)C)=O)CCC(=O)OC(C)(C)C)=O)CC1C=CC=CC=1)=O)CC1C=CC=CC=1)=O.Cl>C(O)(=O)C>[NH:1]1[CH2:45][CH2:44][CH2:43][CH2:42][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:52][C@H:53]([C:59]([NH:61][C@H:62]([C:67]([NH2:69])=[O:68])[CH2:63][CH2:64][S:65][CH3:66])=[O:60])[CH2:54][CH:55]([CH3:56])[CH3:72])=[O:39])[CH2:29][CH2:30][C:31](=[O:37])[OH:32])=[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:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 131713703HLeu-MetNH2 hydrochlorideHCID 131713747BocPro-Phe-Phe-Glu(tBu)NHNH2HCID 131713748BocPro-Phe-Phe-Glu(tBu)-Leu-MetNH22×

Product 1

HCID 131713746HPro-Phe-Phe-Glu-Leu-MetNH2

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocPro-Phe-Phe-Glu(tBu)NHNH2 (0.570 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 0.560 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) have BocPro-Phe-Phe-Glu(tBu)-Leu-MetNH2 in 77% yield. De-t-butylation and de-t-butoxycarbonylation of BocPro-Phe-Phe-Glu(tBu)-Leu-MetNH2 using hydrogen chloride in acetic acid gave HPro-Phe-Phe-Glu-Leu-MetNH2, which was isolated as the amorphous off-white solid hydrochloride salt in 38% yield.

Sources & evidence

ORD record
ord-e8013be172f94f19adf18a6d2432438c
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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