Hydrochloric Acid → HCID 131713711, compound

HRID 2418602Notes

Reaction equation

HRID 2418602 reaction equation
[C:1]([N:8](C)[C@H:9]([C:14]([NH:16][C@H:17]([C:22]([NH2:24])=[O:23])[CH2:18][CH2:19][S:20][CH3:21])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])(OC(C)(C)C)=O.Cl>C(OCC)(=O)C>[NH:8]([CH3:1])[C@H:9]([C:14]([NH:16][C@H:17]([C:22]([NH2:24])=[O:23])[CH2:18][CH2:19][S:20][CH3:21])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713712HCID 131713712, compound

Product 1

HCID 131713711HCID 131713711, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Condensation of BocMeLeuOH (5.0 g.) and HMetNH2 (3.7 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocMeLeu-MetNH2 in 67% yield. De-t-butoxycarbonylation of BocMeLeu-MetNH2 (5.2 g.) using hydrogen chloride in ethyl acetate gave HMeLeu-MetNH2 in 90% yield. Condensation of BocDTrpOPFP (5.60 g.) and HMeLeu-MetHN2 (3.70 g.) by the activated ester method gave BocDTrp-MeLeu-MetNH2 in 55% yield. De-t-butoxycarbonylation of BocDTrp-MeLeu-MetNH2 (3.38 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HDTrp-MeLeu-MetNH2 in 74% yield.

Sources & evidence

ORD record
ord-1cf59259100b451698f7c541871600b7
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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