Hydrochloric Acid → HCID 13386699, compound

HRID 2418537Notes

Reaction equation

HRID 2418537 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][C@@H:6]([C:11]([NH:13][C@H:14]([C:19]([NH2:21])=[O:20])[CH2:15][CH2:16][S:17][CH3:18])=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].Cl>C(O)(=O)C>[NH2:1][CH2:2][C:3]([NH:5][C@@H:6]([C:11]([NH:13][C@H:14]([C:19]([NH2:21])=[O:20])[CH2:15][CH2:16][S:17][CH3:18])=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15602548BocGly-DLeu-MetNH2

Product 1

HCID 13386699HCID 13386699, compoundYield 55%

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-b1d3e7fea37844af85afbb68b0932231
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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