Ethanol → HCID 67675740, compound

HRID 1957007Notes

Reaction equation

HRID 1957007 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:5]([N:7]([CH3:19])[C@@H:8]([C:16](O)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6].[OH-].[Li+].C(O)C.Cl.C[O:31][C:32](=[O:42])[C@H:33]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[NH2:34]>CO.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:5]([N:7]([CH3:19])[C@@H:8]([C:16]([NH:34][C@H:33]([C:32]([OH:31])=[O:42])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 67675222HCID 67675222, compound

Product 1

HCID 67675740HCID 67675740, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Coupling of N-(3,5-dimethylbenzoyl)-N-methyl-(D)-phenylalanine (derived from the corresponding methylester described in example 78 by hydrolysis with lithium hydroxide in methanol/water: [a]D =+88° (c=1.0, ethanol)) with (L)-phenylalanine methyl ester hydrochloride according to example 1 followed by hydrolysis of the methyl ester moiety according to example 12 gives N-(3,5-dimethylbenzoyl)-N-methyl-(D)-phenylalanyl-(L)-phenylalanine; FAB-MS m/e 457 (M-H)-.

Sources & evidence

ORD record
ord-fdc1917da04246bf88078f94deaf0e87
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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