HCID 86590718, compound → HCID 86590719, compound

HRID 1859929Notes

Reaction equation

HRID 1859929 reaction equation
C(OC([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][NH:27][C:28](=[O:41])[C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:31][CH:30]=2)=[CH:20][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])=O)C1C=CC=CC=1>[Pd]>[NH2:11][C@@H:12]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][NH:27][C:28](=[O:41])[C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:33][CH:34]=2)=[CH:22][CH:23]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

3

Reactant 1

HCID 86590718HCID 86590718, compound

Product 1

HCID 86590719HCID 86590719, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a similar manner to that described in Reference example 1(d), a reaction was carried out using methyl (S)-2-benzyloxycarbonylamino-3-[4-[2-(4-pyridine-2-ylbenzoylamino)ethoxy]phenyl]propionate (1.53 g) and palladium on carbon (5%, 150 mg) and the reaction mixture was treated to give methyl (S)-2-amino-3-[4-[2-(4-pyridine-2-ylbenzoylamino)ethoxy]phenyl]propionate (1.14 g). Propyl bromide (0.24 ml) and potassium carbonate (387 mg) were added to a solution of the amine derivative (1.12 g) obtained above in N,N-dimethylformamide (10 ml). The mixture was stirred at 70° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using dichloromethane/methanol=19/1 to give the title compound (196 mg) as colorless crystals.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-27db6ad29b264a3f908c88d04ac16309
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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