Trifluoroacetic acid → HPro-DTrp-Phe-MeDTrp-Leu-MetNH2

HRID 2418620Notes

Reaction equation

HRID 2418620 reaction equation
[N:1]1([C:65](OC(C)(C)C)=O)[CH2:64][CH2:63][CH2:62][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([N:30]([CH3:61])[C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:58]([NH2:60])=[O:59])CCSC)=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=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:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].F[C:73](F)(F)C(O)=O.[CH:79]([SH:82])(S)[CH3:80]>CSC>[NH:1]1[CH2:65][CH2:64][CH2:63][CH2:62][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([N:30]([CH3:61])[C@@H:31]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:58]([NH2:60])=[O:59])[CH2:80][CH2:79][S:82][CH3:73])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=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:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 336451,1-EthanedithiolHCID 131713813HCID 131713813, compound

Product 1

HCID 131713812HPro-DTrp-Phe-MeDTrp-Leu-MetNH2

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Procedure

Condensation of BocPro-DTrp-Phe-MeDTrpNHNH2 (0.840 g.) and HLeu-MetNH2 (0.328 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-DTrp-Phe-MeDTrp-Leu-MetNH2 in 57% yield. De-t-butoxycarbonylation of BocPro-DTrp-Phe-MeDTrp-Leu-MetNH2 (0.450 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HPro-DTrp-Phe-MeDTrp-Leu-MetNH2, which was isolated as the crystalline white solid (m.r. 150°-175° C.) hydrochloride hydrate (3:2) in 59% yield.

Sources & evidence

ORD record
ord-608244333d784260a6bf16cf46565e03
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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