Trifluoroacetic acid → HPro-DTrp-Phe-DTrp-Leu-MeMetNH2

HRID 2418609Notes

Reaction equation

HRID 2418609 reaction equation
N1(C(OC(C)(C)C)=O)CCC[C@H]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([N:52]([CH3:61])[C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54][CH2:55][S:56][CH3:57])=[O:51])CC(C)C)=[O:43])[CH2:32][C:33]1C2C(=CC=CC=2)[NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=CC=CC=2)[NH:10][CH:9]=1)=[O:4].F[C:73](F)(F)[C:74](O)=O>CSC.C(S)(S)C>[NH:30]1[CH2:74][CH2:73][CH2:21][CH2:20][C@H:28]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([NH:30][C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([N:52]([CH3:61])[C@H:53]([C:58]([NH2:60])=[O:59])[CH2:54][CH2:55][S:56][CH3:57])=[O:51])[CH2:16][CH:8]([CH3:9])[CH3:7])=[O:43])[CH2:32][C:33]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:33][CH:32]=[CH:31][CH:42]=2)[NH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131713798BocPro-DTrp-Phe-DTrp-Leu-MeMetNH2

Product 1

HCID 131713799HPro-DTrp-Phe-DTrp-Leu-MeMetNH2

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 336451,1-EthanedithiolSolvent

Procedure

Condensation of BocPro-DTrp-PheOH (Example 33, 1.49 g.) and HDTrp-Leu-MeMetNH2 trifluoroacetate salt (1.25 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocPro-DTrp-Phe-DTrp-Leu-MeMetNH2 in 60% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-DTrp-Leu-MeMetNH2 (1.50 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HPro-DTrp-Phe-DTrp-Leu-MeMetNH2, which was isolated as the amorphous white solid phosphate (1:2) salt dihydrate in 57% yield.

Sources & evidence

ORD record
ord-047d39c8560143bdb0921d56b8f75e37
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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