Methyl L-phenylalaninate hydrochloride → L-Phenylalanine, methyl ester

HRID 1461623Notes

Reaction equation

HRID 1461623 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N1CCC[C@H]1C=O)(OC(C)(C)C)=O>CCOCC.C(Cl)Cl>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6]

Participants

4

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

N-(N-t-butyloxycarbonyl)-5H-pyrrololyl-2-methyl)-L-phenylalanine methyl ester was prepared from L-phenylalanine methyl ester hydrochloride (4.13 mmol) and Boc-prolinal [4.13 mmol, Hamada and Shiori, Chem. Pharm. Bull. (1982) 30, 1921] utilizing the procedure of the first paragraph of Example 9 to yield, after flash chromatography (15-25% Et2O/CH2Cl2 ; SiO2 gel), 0.588 g (40% yield) of pure product.

Workup

  1. customto yield

Sources & evidence

ORD record
ord-d0b59b4a531f4153aa289b08552b3469
Source dataset
uspto-grants-1991_12
Patent number
US05075451

Reaction notes

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