BocPro-Phe-Phe-PheNHNH2 → BocPro-Phe-Phe-Gly-Leu-NleNH2

HRID 2418554Notes

Reaction equation

HRID 2418554 reaction equation
[N:1]1([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:28]([C:36]([NH:38]N)=[O:37])CC1C=CC=CC=1)=[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].NCC(N[C@H:55]([C:60]([NH:62][C@H:63]([C:68]([NH2:70])=[O:69])[CH2:64][CH2:65][CH2:66][CH3:67])=[O:61])[CH2:56][CH:57]([CH3:59])[CH3:58])=O>>[N:1]1([C:43]([O:45][C:46]([CH3:48])([CH3:49])[CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][CH2:28][C:36]([NH:38][C@H:55]([C:60]([NH:62][C@H:63]([C:68]([NH2:70])=[O:69])[CH2:64][CH2:65][CH2:66][CH3:67])=[O:61])[CH2:56][CH:57]([CH3:58])[CH3:59])=[O:37])=[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]

Participants

3

Reactant 2

HCID 131713724BocPro-Phe-Phe-PheNHNH2HCID 131713725HCID 131713725, compound

Product 1

HCID 131713723BocPro-Phe-Phe-Gly-Leu-NleNH2Yield 69%

Procedure

Condensation of BocPro-Phe-Phe-PheNHNH2 (Example 1, 1.09 g.) and HGly-Leu-NleNH2 (0.70 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-Phe-Phe-Gly-Leu-NleNH2 in 69% yield. De-t-butoxycarbonylation of BocPro-Phe-Phe-Gly-Leu-NleNH2 (1.0 g.) using hydrogen chloride in acetic acid gave HPro-Phe-Phe-Gly-Leu-NleNH2, which was isolated as the amorphous white solid phosphate (1:1) salt sesquihydrate in 65% yield.

Sources & evidence

ORD record
ord-f46daf0a4cf84ac9bdead3a994934f86
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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