Hydrochloric Acid → HPro-Phe-Phe-Gly-Leu-DMetNH2

HRID 2418546Notes

Reaction equation

HRID 2418546 reaction equation
[N:1]1([C:51](OC(C)(C)C)=O)[CH2:50][CH2:49][CH2:48][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:32]([C:37]([NH:39][C@@H:40]([C:45]([NH2:47])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])=[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[CH2:51][CH2:50][CH2:49][CH2:48][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:32]([C:37]([NH:39][C@@H:40]([C:45]([NH2:47])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])=[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713716HCID 131713716, compound

Product 1

HCID 131713717HPro-Phe-Phe-Gly-Leu-DMetNH2

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocPro-Phe-PheNHNH2 (Example 1, 1.93 g.) and HGly-Leu-DMetNH2 (1.31 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-Phe-Phe-Gly-Leu-DMetNH2 in 60% yield. De-t-butoxycarbonylation of BocPro-Phe-Phe-Gly-Leu-DMetNH2 (1.6 g.) using hydrogen chloride in acetic acid gave HPro-Phe-Phe-Gly-Leu-DMetNH2, which was isolated as the amorphous white solid phosphate (1:1) slat sesquihydrate in 72% yield.

Sources & evidence

ORD record
ord-6df1312bebc94708b73d56f4f955cbed
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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