Acetic Acid → O-[(butylamino)carbonyl]-2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide, monohydrochloride

HRID 2291750Notes

Reaction equation

CC(C)(OC([NH:7][C@H:8]([C:19]([NH:21][C@@H:22]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:25])[CH3:23])=[O:20])[CH2:9][C:10]1[C:15]([CH3:16])=[CH:14]C(O)=C[C:11]=1[CH3:18])=O)C.[NH2:37][C@@H:38](C(O)=O)[CH2:39][C:40]1C=CC(O)=C[CH:41]=1.[ClH:50].O1[CH2:56][CH2:55][O:54][CH2:53]C1.C(O)(=[O:59])C>>[ClH:50].[CH2:38]([NH:37][C:53]([O:54][C:55]1[CH:56]=[C:11]([CH3:18])[C:10]([CH2:9][C@@H:8]([C:19]([NH:21][C@@H:22]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:25])[CH3:23])=[O:20])[NH2:7])=[C:15]([CH3:16])[CH:14]=1)=[O:59])[CH2:39][CH2:40][CH3:41]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 71098D-Tyrosine

HCID 13656661N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-tyrosyl-N-(3-phenylpropyl)-D-alaninamide

HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 131715818O-[(butylamino)carbonyl]-2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide, monohydrochloride

Procedure

The Boc-precursor of the titled compound is prepared by the method of Example 6 using N[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide in place of its D-tyrosine containing analog. The resulting Boc-precursor is reacted with glacial acetic acid and 6.8N HCl-dioxane according to the method of Example 3 to produce the titled hydrochloride salt.

Sources & evidence

ORD record: ord-9ff3a9e10b24406ab67cd1b2056f5e3d
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04797470

Reaction notes

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