Water → HCID 53919526, compound

HRID 1419510Notes

Reaction equation

HRID 1419510 reaction equation
[C:1]([NH:5][C:6]([C:8]1[N:9]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:10][CH2:11][NH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].[C:23](Cl)(=[O:25])[CH3:24].O>C(OCCCC)(=O)C.C(#N)C.C(OCCCC)(=O)C>[C:1]([NH:5][C:6]([C:8]1[N:9]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:10][CH2:11][N:12]([C:23](=[O:25])[CH3:24])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 67579363HCID 67579363, compound

Product 1

HCID 53919526HCID 53919526, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 31272Butyl AcetateSolventHCID 86753986HCID 86753986, compoundSolvent

Conditions

Temperature
50 °C

Procedure

168.7 g (0.705 mol) of 1-propionyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide was placed in 1.92 l of a butyl acetate/acetonitrile mixture (4:1). The suspension was heated to 50° C. and 68.2 g (0.812 mol) of sodium hydrogen carbonate was added. A solution of 57.0 g (0.726 mol) of acetyl chloride in 120 ml of butyl acetate was added dropwise over 30 minutes. The reaction mixture was then stirred for a further 40 minutes at 50° C. 190 ml of water was added cautiously and the aqueous phase was separated off and re-extracted with 200 ml of butyl acetate at 50° C. The combined organic extracts were concentrated to 1100 ml and cooled slowly to 2° C. to induce crystallization. The solid was filtered off and rewashed with 100 ml of cold butyl acetate. Recrystallization from 700 ml of butyl acetate gave 183.8 g (92.7%) of the title compound in the form of white crystals. The melting point of the title compound was: 133.5° to 134.6° C. Other data concerning the title compound was:

Workup

  1. customthe aqueous phase was separated off
  2. extractionre-extracted with 200 ml of butyl acetate at 50° C
  3. concentrationThe combined organic extracts were concentrated to 1100 ml
  4. temperaturecooled slowly to 2° C.
  5. customcrystallization
  6. filtrationThe solid was filtered off
  7. customRecrystallization from 700 ml of butyl acetate

Sources & evidence

ORD record
ord-a3cf718802b94d67a907c4d1ac09aea4
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

Loading…