DL-Tyrosine → HCID 131715817, compound

HRID 2291749Notes

Reaction equation

HRID 2291749 reaction equation
NC(C(O)=O)CC1C=CC(O)=CC=1.[CH3:14][C:15]1[CH:40]=[C:39]([O:41][C:42]([NH:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:43])[CH:38]=[C:37]([CH3:51])[C:16]=1[CH2:17][C@@H:18]([C:20]([NH:22][C@@H:23]([C:25]([NH:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26])[CH3:24])=[O:21])[NH2:19].[ClH:52].O1CCOCC1>C(O)(=O)C>[ClH:52].[CH3:14][C:15]1[CH:40]=[C:39]([O:41][C:42]([NH:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:43])[CH:38]=[C:37]([CH3:51])[C:16]=1[CH2:17][C@@H:18]([C:20]([NH:22][C@@H:23]([C:25]([NH:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26])[CH3:24])=[O:21])[NH2:19]

Participants

5

Reactant 3

HCID 1153DL-TyrosineHCID 14373516HCID 14373516, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 131715817HCID 131715817, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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

Sources & evidence

ORD record
ord-5f52d731aa20414fb579b077bd2ea4af
Source dataset
uspto-grants-1989_01
Patent number
US04797470

Reaction notes

Loading…