Hydrochloric Acid → HDLeu-MetNH2

HRID 2418535Notes

Reaction equation

HRID 2418535 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH2:17])=[O:16])[CH2:11][CH2:12][S:13][CH3:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl>C(O)(=O)C>[NH2:1][C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH2:17])=[O:16])[CH2:11][CH2:12][S:13][CH3:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13334463BocDLeu-MetNH2

Product 1

HCID 12952804HDLeu-MetNH2Yield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocDLeuOH (2.49 g.) and HMetNH2 (1.85 g.) by the mixed anhydride method using isobutyl chloroformate gave BocDLeu-MetNH2 in 47% yield. De-t-butoxycarbonylation of BocDLeu-MetNH2 (1.70 g.) using hydrogen chloride in acetic acid gave HDLeu-MetNH2 in 78% yield. Condensation of BocGlyOSu (1.8 g.) and HDLeu-MetNH2 (1.0 g.) by the activated ester method gave BocGly-DLeu-MetNH2 in 95% yield. De-t-butoxycarbonylation of BocGly-DLeu-MetNH2 (1.35 g.) using hydrogen chloride in acetic acid gave HGly-DLeu-MetNH2 in 55% yield.

Sources & evidence

ORD record
ord-b5ac6ca2050b428fbf05ed5dc2d4a58b
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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