Pivalaldehyde → N-neopentylidene-L-alanine ethyl ester

HRID 47595

Reaction equation

HRID 47595 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[CH:15](=O)[C:16]([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:8])[C@H:5]([CH3:7])[N:6]=[CH:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 76507L-Alanine ethyl ester

Product 1

HCID 11412788N-neopentylidene-L-alanine ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Step-2. L-Alanine ethyl ester from step-1 (9 g) was dissolved in 150 ml anhydrous CH2Cl2. The solution was cooled to 0° C. MgSO4 (10.17 g) was added to the solution followed by addition of pivalaldehyde (6.95 g). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was filtered and the filtrate was evaporated to give 11.2 g of N-neopentylidene-L-alanine ethyl ester. The product was used for next step without further purification. MS: 186 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ab9b76fdbc7743159f62fc351f2ad4f3
Source dataset
uspto-grants-2004_03
Patent number
US06699888B2

Linked notes

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