Methyl (2Z)-2-acetamido-3-(naphthalen-2-yl)prop-2-enoate → methyl N-acetyl-3-(2-naphthyl)-D-alaninate

HRID 1585233Notes

Reaction equation

HRID 1585233 reaction equation
[C:1]([NH:4]/[C:5](=[CH:10]\[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)/[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]>CO>[CH3:9][O:8][C:6](=[O:7])[C@@H:5]([CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 15168117Methyl (2Z)-2-acetamido-3-(naphthalen-2-yl)prop-2-enoate

Product 1

HCID 9878585methyl N-acetyl-3-(2-naphthyl)-D-alaninateYield 102.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (Z)-2acetamido-3-(2-naphthyl)propenoate (0.3 g, 1.11 mmol) and the catalyst (I) (7 mg, 0.011 mmol, 1.0 mol %) in degassed methanol (10 ml) was placed in a 50 ml Parr pressure reactor purged with nitrogen. The vessel was then purged with hydrogen (×3) and charged to 4.13 MPa (600 psi) of hydrogen. After stirring for 2 h, the solution was evaporated to give (R)-N-acetyl-3(2-naphthyl)alanine methyl ester (0.31 g, quantitative yield, 77.5% ee).

Workup

  1. custompurged with nitrogen
  2. customThe vessel was then purged with hydrogen (×3)
  3. additioncharged to 4.13 MPa (600 psi) of hydrogen
  4. customthe solution was evaporated

Sources & evidence

ORD record
ord-f645e8cca3c94674b6c1e958ac501be0
Source dataset
uspto-grants-1999_08
Patent number
US05936109

Reaction notes

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