Dichloromethane → L-Alanine 1,1-dimethylethyl ester

HRID 496237Notes

Reaction equation

HRID 496237 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH3:4].C(Cl)Cl.CC(C=O)(C)C>CCOCC>[NH2:2][C@H:3]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12417PivalaldehydeHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 89016L-Alanine 1,1-dimethylethyl esterYield 147.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 25.0 g (0.14 mol) alanine, tert-butyl ester hydrochloride, 20.0 g of 4 Å powdered molecular sieves, 21 mL (0.15 mol) of TEA and 400 mL of dry CH2Cl2 was added 18 mL (0.16 mol) of pivaldehyde. The mixture was stirred at rt for 17 h, diluted with 1 L of Et2O, filtered through a pad of celite and concentrated in vacuo to give 30 g (˜100%) of alanine, tert-butyl ester, tert-butyl imine as a colorless oil which was used without further purification.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d5caabdd929498eb1bc56eb255c821e
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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