Trifluoroacetic acid → HDTrp-Leu-MeNleNH2

HRID 2418622Notes

Reaction equation

HRID 2418622 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([N:23]([CH3:32])[C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][CH2:27][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]([NH:15][C@H:16]([C:21]([N:23]([CH3:32])[C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:19])[CH3:20])=[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 131713814BocDTrp-Leu-MeNleNH2

Product 1

HCID 131713815HDTrp-Leu-MeNleNH2Yield 37%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 336451,1-EthanedithiolSolvent

Procedure

Condensation of BocDTrp-LeuOH (Example 38, 2.09 g.) and MeNleNH2 (1.00 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocDTrp-Leu-MeNleNH2 in 99% yield. De-t-butoxycarbonylation of BocDTrp-Leu-MeNleNH2 (2.50 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HDTrp-Leu-MeNleNH2 in 37% yield.

Sources & evidence

ORD record
ord-1e3cb4d3d4614011b0c1bcb9efd31140
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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