Hydrochloric Acid → HPro-Phe-Phe-Gly-MeLeu-MetNH2

HRID 2418542Notes

Reaction equation

HRID 2418542 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]([NH:27][CH2:28][C:29]([N:31]([CH3:48])[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[CH2:52][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]([NH:27][CH2:28][C:29]([N:31]([CH3:48])[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: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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713714HCID 131713714, compound

Product 1

HCID 131713713HPro-Phe-Phe-Gly-MeLeu-MetNH2Yield 36%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocPro-Phe-Phe-GlyOH (2.8 g.) and MeLeu-MetNH2 (1.6 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-Phe-Phe-Gly-MeLeu-MetNH2 in 49% yield. De-t-butoxycarbonylation of BocPro-Phe-Phe-GlyMeLeu-MetNH2 using hydrogen chloride in acetic acid gave HPro-Phe-Phe-Gly-MeLeu-MetNH2, which was isolated as the amorphous white solid free base in 36% yield.

Sources & evidence

ORD record
ord-6aaf950c323e4792bac37a19be1a18ea
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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