Hydrochloric Acid → HCID 92259190, compound

HRID 2418544Notes

Reaction equation

HRID 2418544 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 131713715BocGly-Leu-DMetNH2

Product 1

HCID 92259190HCID 92259190, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of BocLeuOH (3.49 g.) and HDMetNH2 (2.0 g.) by the mixed anhydride method using isobutyl chloroformate gave BocLeu-DMetNH2 in 70% yield. De-t-butoxycarbonylation of BocLeu-DMetNH2 (2.74 g.) using hydrogen chloride in ethyl acetate gave HLeu-DMetNH2 in 91% yield. Condensation of BocGlyOSu (2.66 g.) and HLeu-DMetNH2 (1.95 g.) by the active ester method gave BocGly-Leu-DMetNH2 in 92% yield. De-t-butoxycarbonylation of BocGly-Leu-DMetNH2 (2.30 g.) using hydrogen chloride in acetic acid gave HGly-Leu-DMetNH2 in 79% yield.

Sources & evidence

ORD record
ord-ef36ea4761ad4e6ea5e44f9a62b4217f
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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