Trifluoroacetic acid → HCID 131713736, compound

HRID 2418564Notes

Reaction equation

HRID 2418564 reaction equation
[N:1]1([C:53](OC(C)(C)C)=O)[CH2:52][CH2:51][CH2:50][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]([CH3:49])[C@H:17]([C:25]([N:27]([CH2:29][C:30]([NH:32][C@H:33]([C:38]([NH:40][C@H:41]([C:46]([NH2:48])=[O:47])[CH2:42][CH2:43][S:44][CH3:45])=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])C)=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]1[CH2:53][CH2:52][CH2:51][CH2:50][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]([CH3:49])[C@H:17]([C:25]([NH:27][CH2:29][C:30]([NH:32][C@H:33]([C:38]([NH:40][C@H:41]([C:46]([NH2:48])=[O:47])[CH2:42][CH2:43][S:44][CH3:45])=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])=[O:26])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131713737HCID 131713737, compound

Product 1

HCID 131713736HCID 131713736, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Condensation of BocPro-Phe-MePheNHNH2 (0.86 g.) and HSar-Leu-MetNH2 (Example 3, 0.63 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-Phe-MePhe-Sar-Leu-MetNH2 in 75% yield. De-t-butoxycarbonylation of BocPro-Phe-MePhe-Sar-Leu-MetNH2 (0.90 g.) using trifluoroacetic acid in methylene dichloride gave HPro-Phe-MePhe-Gly-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt in 59% yield.

Sources & evidence

ORD record
ord-3df8c4aa9888401098c4034dd6a037ce
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

Loading…