Butylamine → Tert-butyl 2-(butylamino)acetate

HRID 838961Notes

Reaction equation

HRID 838961 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].Cl[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>>[C:11]([O:10][C:8](=[O:9])[CH2:7][NH:5][CH2:1][CH2:2][CH2:3][CH3:4])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 66052tert-Butyl chloroacetate

Product 1

HCID 22768716Tert-butyl 2-(butylamino)acetateYield 90.9%

Procedure

To 36.5 g of butylamine was added with stirring 15.05 g of tert-butyl chloroacetate over a period of 30 minutes, while maintaining the temperature at 30°-70° C. The reaction mixture was held at 70° C for an additional 1 hour. At the end of this period, the excess butyl amine was evaporated in vacuo, and the residue was taken up in 40 ml of 2N NaOH solution and 50 ml of benzene, transferred into a separatory funnel and well shaken. The benzene solution was separated, washed with water, dried over anhydrous sodium sulfate and filtered. After evaporation of benzene, the residue was distilled under reduced pressure to give 17.0 g (90.9 percent) of N-butylglycine tert-butyl ester, B.P. 76° C/4 mmHg.

Workup

  1. temperaturewhile maintaining the temperature at 30°-70° C
  2. customAt the end of this period, the excess butyl amine was evaporated in vacuo
  3. custom50 ml of benzene, transferred into a separatory funnel
  4. customThe benzene solution was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customAfter evaporation of benzene
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-d651a32cf28648afaf9c5e541dbda2fc
Source dataset
uspto-grants-1978_06
Patent number
US04093712

Reaction notes

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