Trifluoroacetic acid → HDTrp-Leu-MeMetNH2 trifluoroacetate

HRID 2418607Notes

Reaction equation

HRID 2418607 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][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.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>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][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.[F:40][C:41]([C:42]([OH:44])=[O:43])([F:46])[F:45]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131713797BocDTrp-Leu-MeMetNH2

Product 1

HCID 131713795HDTrp-Leu-MeMetNH2 trifluoroacetateYield 79%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 336451,1-EthanedithiolSolvent

Procedure

Condensation of BocLeuOH (5.00 g.) and HMeMetNH2 (4.00 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocLeu-MeMetNH2 in 81% yield. De-t-butoxycarbonylation of BocLeu-MeMetNH2 (5.96 g.) using hydrogen chloride in ethyl acetate gave HLeu-MeMetNH2 hydrochloride salt in 98% yield. Condensation of BocDTrpOPFP (7.56 g.) and HLeu-MeMetNH2 hydrochloride salt (5.00 g.) by the activated ester method gave BocDTrp-Leu-MeMetNH2 in 56% yield. De-t-butoxycarbonylation of BocDTrp-Leu-MeMetNH2 (2.0 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HDTrp-Leu-MeMetNH2 trifluoroacetate salt in 79% yield.

Sources & evidence

ORD record
ord-3c827f71ffbd42c28f1f52fd3dfe46be
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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