Trifluoroacetic acid → HDTrp-MeLeu-MetNH2

HRID 2418603Notes

Reaction equation

HRID 2418603 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([N:15]([CH3:32])[C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.FC(F)(F)C(O)=O>CSC.C(S)(S)C>[NH2:1][C@@H:2]([C:13]([N:15]([CH3:32])[C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131713792BocDTrp-MeLeu-MetNH2

Product 1

HCID 131713791HDTrp-MeLeu-MetNH2Yield 74%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 336451,1-EthanedithiolSolvent

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-632ed560a22b413188b23376104d7628
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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