Hydrochloric Acid → HCID 131713751, compound

HRID 2418573Notes

Reaction equation

HRID 2418573 reaction equation
N1(C(OC(C)(C)C)=O)CCC[C@H]1C([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[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.[OH:42][CH:43]1[O:51][C@H:50]([CH2:52][OH:53])[C@H:48]([OH:49])[C@H:46]([OH:47])[C@H:44]1[OH:45].[NH2:54][C@H:55]([C:60]([NH2:62])=[O:61])[CH2:56][CH2:57][S:58][CH3:59].Cl>C(O)(=O)C>[NH:54]1[CH2:43][CH2:44][CH2:46][CH2:48][C@H:50]1[C:52]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[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:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:53].[OH:42][CH:43]1[O:51][C@H:50]([CH2:52][OH:53])[C@H:48]([OH:49])[C@H:46]([OH:47])[C@H:44]1[OH:45].[NH2:54][C@H:55]([C:60]([NH2:62])=[O:61])[CH2:56][CH2:57][S:58][CH3:59]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713753HCID 131713753, compound

Product 1

HCID 131713751HCID 131713751, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocPro-Phe-Phe-GlyOH (1.61 g.) and HGal-MetNH2 dihydrochloride salt (0.70 g.) using dicyclohexylcarbodiimide and 4-dimethylaminopyridine as catalyst gave BocPro-Phe-Phe-Gly-Gal-MetNH2 in 28% yield. De-t-butoxycarbonylation of BocPro-Phe-Phe-Gly-Gal-MetNH2 (0.44 g.) using hydrogen chloride in acetic acid gave HPro-Phe-Phe-Gly-Gal-MetNH2, which was isolated as the amorphous white solid dihydrochloride acetate salt hydrate in 35% yield.

Sources & evidence

ORD record
ord-8de528dfaf4a4dde841ac2f27c6ab83c
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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