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

HRID 133341Notes

Reaction equation

HRID 133341 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 AA 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 AQ above using isobutanol to provide the title compound. Purification was by preparative plate chromatography.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-f25257d46392416f919af8dead4e6188
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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