Potassium Carbonate → N-(1-Amino-1-oxobutan-2-yl)-4-chlorobutanamide, (S)-

HRID 1904198Notes

Reaction equation

HRID 1904198 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][C@@H:9]([CH2:13][CH3:14])[C:10]([NH2:12])=[O:11].[Cl:15][CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C(#N)C.CCOCC>[NH2:12][C:10]([C@@H:9]([NH:8][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][Cl:15])[CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 11961924(2S)-2-Aminobutanamide hydrochloride

Product 1

HCID 29938341N-(1-Amino-1-oxobutan-2-yl)-4-chlorobutanamide, (S)-Yield 78.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

345.6 g (2.5 moles) of ground potassium carbonate are mixed with 138.5 g (1 mole) of (S)-2-amino-butanamide hydrochloride in 2.5 liters of acetonitrile. The reaction mixture is cooled to 0° C. and a solution of 129.2 g (1.2 mole) of 4-chlorobutyryl chloride in 500 ml of acetonitrile is introduced dropwise. After the addition, the reaction mixture is allowed to return to ambient temperature; the insoluble matter is filtered off and the filtrate evaporated under reduced pressure. The crude residue obtained is stirred in 1.2 liter of anhydrous ether for 30 minutes at a temperature between 5° and 10° C. The precipitate is filtered off, washed twice with 225 ml of ether and dried in vacuo to obtain 162.7 g of (S)-N-[1-(aminocarbonyl)propyl]-4-chlorobutanamide.

Workup

  1. additionAfter the addition
  2. customto return to ambient temperature
  3. filtrationthe insoluble matter is filtered off
  4. customthe filtrate evaporated under reduced pressure
  5. customThe crude residue obtained
  6. filtrationThe precipitate is filtered off
  7. washwashed twice with 225 ml of ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-069dcf33376f41e393ee9a23e3492ac6
Source dataset
uspto-grants-1989_06
Patent number
US04837223

Reaction notes

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