Pivalaldehyde → HCID 10797610, compound

HRID 1747224Notes

Reaction equation

HRID 1747224 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH:6]([CH3:8])[NH2:7])[CH3:3].[CH:10](=O)[C:11]([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[CH3:10][C:11]([CH3:14])([CH3:13])[CH:12]=[N:7][CH:6]([CH3:8])[C:5]([O:4][CH2:2][CH3:3])=[O:9]

Participants

4

Reactant 2

HCID 12417PivalaldehydeHCID 102560Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 10797610HCID 10797610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of DL-alanine ethyl ester hydrochloride (10 g, 65.1 mmol) in DCM (150 mL) was washed with 2M aq. NaOH and the layers were separated. The organic phase was dried over Na2SO4, filtered and the filtrate was cooled to 0° C. before MgSO4 hydrate (11.3 g) followed by pivalaldeyde (7.72 g, 89.6 mmol) were added and the resulting mixture was warmed to RT and stirred for 16 h. The reaction mixture was filtered and evaporated in vacuo to give rac-ethyl 2-((2,2-dimethylpropylidene)amino)propanoate that was used further without purification.

Workup

  1. washwas washed with 2M aq. NaOH
  2. customthe layers were separated
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. additionwere added
  6. temperaturethe resulting mixture was warmed to RT
  7. filtrationThe reaction mixture was filtered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-238f9de28fa546ad9269e42d5176ec44
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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