Dimethylformamide → HCID 76114879, compound

HRID 275645Notes

Reaction equation

HRID 275645 reaction equation
[C:1]([NH:4][CH:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:6][C:7]1[CH:12]=C[CH:10]=[C:9](N)[CH:8]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.CI.ClCCl.[CH3:31][N:32]([CH:34]=O)[CH3:33]>>[C:1]([NH:4][CH:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:34]([N:32]([CH3:31])[CH3:33])[CH:12]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 6328Methyl iodide2×HCID 6344DichloromethaneHCID 8471Triethylamine2×HCID 76113955HCID 76113955, compound

Product 1

HCID 76114879HCID 76114879, compound

Conditions

Temperature
30 °C

Procedure

4 g of ethyl (RS)-N-acetyl-3-aminophenylalaninate, prepared as described in Example 35-8, in 15 ml of DMF are placed in a three-necked flask under a nitrogen atmosphere, and 5.5 ml of triethylamine, and then 2.5 ml of methyl iodide and 4 ml of dichloromethane, are added while maintaining the temperature in the region of 30° C. using an icebath. The mixture is then warmed at 35° C. for 18 h. 1 ml of methyl iodide dissolved in 1 ml of DMF is then added slowly while maintaining the temperature in the region of 30° C.; 2.2 ml of triethylamine are then added and the mixture is subsequently warmed for a further 5 h at 35° C. The mixture is brought to room temperature and then extracted with 100 ml of ethyl acetate and 150 ml of distilled water. The aqueous phase is separated off after settling and then rewashed with 2 times 70 ml of ethyl acetate. The organic phases are combined, washed with 2 times 80 ml of distilled water and then with 50 ml of distilled water which is saturated with NaCl. The organic phase is separated off after settling, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure in order to yield 2.4 g of a product which is purified by flash chromatography (dichloromethane, MeOH 90/10). 0.72 g (16%) of ethyl (RS)-3-N-acetyl-3-dimethylamino phenylalaninate is thus obtained in the form of yellow crystals.

Workup

  1. customare placed in a three-necked flask under a nitrogen atmosphere
  2. temperatureThe mixture is then warmed at 35° C. for 18 h
  3. additionis then added slowly
  4. temperaturewhile maintaining the temperature in the region of 30° C.
  5. temperaturethe mixture is subsequently warmed for a further 5 h at 35° C
  6. customis brought to room temperature
  7. extractionextracted with 100 ml of ethyl acetate and 150 ml of distilled water
  8. customThe aqueous phase is separated off
  9. washwashed with 2 times 80 ml of distilled water
  10. customThe organic phase is separated off
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure in order

Sources & evidence

ORD record
ord-29ad437df09146e9b57e39515bc9514d
Source dataset
uspto-grants-2002_03
Patent number
US06352839B1

Reaction notes

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