Methyl pyruvate → N-(3,4-ethylenedioxyphenyl)alanine Iso-butyl Ester

HRID 2184890Notes

Reaction equation

HRID 2184890 reaction equation
[C:1](OC)(=O)[C:2]([CH3:4])=O.[CH3:8][O:9][C:10](=[O:24])[C@H:11]([CH3:23])[NH:12][C:13]1[CH:18]=[CH:17][C:16]2[O:19][CH2:20][CH2:21][O:22][C:15]=2[CH:14]=1>C(O)C(C)C>[CH2:8]([O:9][C:10](=[O:24])[C@H:11]([CH3:23])[NH:12][C:13]1[CH:18]=[CH:17][C:16]2[O:19][CH2:20][CH2:21][O:22][C:15]=2[CH:14]=1)[CH:2]([CH3:4])[CH3:1]

Participants

4

Reactant 2

HCID 11748Methyl pyruvateHCID 53867794N-(3,4-ethylenedioxyphenyl)alanine methyl ester

Product 1

HCID 53856555N-(3,4-ethylenedioxyphenyl)alanine Iso-butyl Ester

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

Following reductive amination General Procedure A above and using 1,4-benzodioxa-6-amine (Aldrich) and methyl pyruvate (Aldrich), N-(3,4-ethylenedioxyphenyl)alanine methyl ester was prepared. The methyl ester was then transesterified following General Procedure Q above using isobutanol to provide the title compound. Purification was by preparative plate chromatography.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-7af2f8d4d07d4af8a2ef7eda1470acaf
Source dataset
uspto-grants-2002_06
Patent number
US06399628B1

Reaction notes

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