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

HRID 2418534Notes

Reaction equation

HRID 2418534 reaction equation
[N:1]1([C:52](OC(C)(C)C)=O)[CH2:51][CH2:50][CH2:49][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([N:27]([CH2:29][C:30]([NH:32][C@H:33]([C:38]([NH:40][C@H:41]([C:46]([NH2:48])=[O:47])[CH2:42][CH2:43][S:44][CH3:45])=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])[CH3:28])=[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[CH2:52][CH2:51][CH2:50][CH2:49][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([N:27]([CH2:29][C:30]([NH:32][C@H:33]([C:38]([NH:40][C@H:41]([C:46]([NH2:48])=[O:47])[CH2:42][CH2:43][S:44][CH3:45])=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])[CH3:28])=[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:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713708HCID 131713708, compound

Product 1

HCID 131713707HPro-Phe-Phe-Sar-Leu-MetNH2

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocPro-Phe-PheNHNH2 (Example 1, 1.35 g.) and HSar-Leu-MetNH2 (0.95 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-Phe-Phe-Sar-Leu-MetNH2 in 45% yield. De-t-butoxycarbonylation of BocPro-Phe-Phe-Sar-Leu-MetNH2 (0.90 g.) using hydrogen chloride in acetic acid gave HPro-Phe-Phe-Sar-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt sesquihydrate in 59% yield.

Sources & evidence

ORD record
ord-3f4ba1cd3e47443eb6dc3562d5dd6ff5
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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