Hydrochloric Acid → HPro-DPhg-Phe-DPhe-Leu-MetNH2

HRID 2418590Notes

Reaction equation

HRID 2418590 reaction equation
[N:1]1([C:57](OC(C)(C)C)=O)[CH2:56][CH2:55][CH2:54][C@H:2]1[C:3]([NH:5][C@@H:6]([C:13]([NH:15][C@H:16]([C:24]([NH:26][C@@H:27]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:51]([NH2:53])=[O:52])[CH2:47][CH2:48][S:49][CH3:50])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:36])[CH2:28]C1C=CC=CC=1)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl>C(OCC)(=O)C>[NH:1]1[CH2:57][CH2:56][CH2:55][CH2:54][C@H:2]1[C:3]([NH:5][C@@H:6]([C:13]([NH:15][C@H:16]([C:24]([NH:26][C@@H:27]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:51]([NH2:53])=[O:52])[CH2:47][CH2:48][S:49][CH3:50])=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])=[O:36])[CH2:28][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713775HCID 131713775, compound

Product 1

HCID 131713774HPro-DPhg-Phe-DPhe-Leu-MetNH2

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Condensation of BocPro-DPhg-PheNHNH2 (1.27 g.) and HDPhe-Leu-MetNH2 hydrochloride salt (Example 23, 1.11 g.) by the acyl azide method (Yajima et al., Chem. Pharm. Bull., vol. 19, p. 1900, 1971) gave BocPro-DPhg-Phe-Dphe-Leu-MetNH2 in 89% yield. De-t-butoxycarbonylation of BocPro-DPhg-Phe-DPhe-Leu-MetNH2 (1.67 g.) using hydrogen chloride in ethyl acetate gave HPro-DPhg-Phe-DPhe-Leu-MetNH2, which was isolated as the amorphous white solid phosphate (1:1) salt pentahydrate in 12% yield.

Sources & evidence

ORD record
ord-7550bc3bfbe34aadae874c3ec6e1b2df
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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