Hydrochloric Acid → HDPhe-Leu-MetNH2 hydrochloride

HRID 2418586Notes

Reaction equation

HRID 2418586 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:26]([NH2:28])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:36]>C(OCC)(=O)C>[NH2:1][C@@H:2]([C:10]([NH:12][C@H:13]([C:18]([NH:20][C@H:21]([C:26]([NH2:28])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[ClH:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713767BocDPhe-Leu-MetNH2

Product 1

HCID 131713768HDPhe-Leu-MetNH2 hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Condensation of BocDPheOH (2.65 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 2.98 g.) by the mixed anhydride method using isobutyl chloroformate gave BocDPhe-Leu-MetNH2 in 57% yield. De-t-butoxycarbonylation of BocDPhe-Leu-MetNH2 (2.7 g.) using hydrogen chloride in ethyl acetate gave HDPhe-Leu-MetNH2 hydrochloride salt in 82% yield.

Sources & evidence

ORD record
ord-06047177a7764c63ad9f21c85d9b39c5
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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