BocPro-DPhe-PheNHNH2 → BocPro-DPhe-Phe-Trp-Leu-MetNH2

HRID 2418566Notes

Reaction equation

HRID 2418566 reaction equation
[N:1]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][CH2:29][C@H:2]1[C:3]([NH:5][C@@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27]N)=[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].N[C@H:40]([C:51]([NH:53][C@H:54]([C:59]([NH:61][C@H:62]([C:67]([NH2:69])=[O:68])[CH2:63][CH2:64][S:65][CH3:66])=[O:60])[CH2:55][CH:56]([CH3:58])[CH3:57])=[O:52])[CH2:41][C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:44][CH:43]=1>>[N:1]1([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31][CH2:30][CH2:29][C@H:2]1[C:3]([NH:5][C@@H:6]([C:14]([NH:16][C@H:17]([C:25]([NH:27][C@H:40]([C:51]([NH:53][C@H:54]([C:59]([NH:61][C@H:62]([C:67]([NH2:69])=[O:68])[CH2:63][CH2:64][S:65][CH3:66])=[O:60])[CH2:55][CH:56]([CH3:57])[CH3:58])=[O:52])[CH2:41][C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:44][CH:43]=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]

Participants

3

Reactant 2

HCID 131713729BocPro-DPhe-PheNHNH2HCID 131713741HTrp-Leu-MetNH2

Product 1

HCID 131713740BocPro-DPhe-Phe-Trp-Leu-MetNH2Yield 97%

Procedure

Condensation of BocPro-DPhe-PheNHNH2 (Example 9, 477 mg.) and HTrp-Leu-MetNH2 (510 mg.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-DPhe-Phe-Trp-Leu-MetNH2 in 97% yield. De-t-butoxycarbonylation of BocPro-DPhe-Phe-Trp-Leu-MetNH2 (0.80 g.) using trifluoroacetic acid containing 10% water gave HPro-DPhe-Phe-DTrp-Leu-MetNh2, which was isolated as the amorphous white solid phosphate (1:2) salt tetrahydrate in 32% yield.

Sources & evidence

ORD record
ord-b643f50b70b549389a31baf28365044e
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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