Potassium Carbonate → (R)-N-[1-(aminocarbonyl)propyl]-4-chlorobutanamide

HRID 2309707Notes

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]>CC(C)=O.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

Conditions

Temperature: 0 °C

Procedure

31.1 g (0.225 mole) of ground potassium carbonate are mixed with 12.47 g (0.09 mole) of (R)-2-aminobutanamide hydrochloride in 160 ml of acetone. The reaction mixture is cooled to 0° C. and a solution of 15.23 g (0.108 mole) of 4-chlorobutyryl chloride in 25 ml of acetone 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 100 ml of anhydrous ether for 15 minutes at a temperature between 5° and 10° C. The precipitate is filtered off, washed twice with 30 ml of ether, and dried in vacuo to obtain 16 g of (R)-N-[1-(aminocarbonyl)propyl]-4-chlorobutanamide. Melting point: 127°-129° C. [alpha]D25 : +22.2° (c=1, methanol). Yield: 86%.

Workup

additionAfter the addition
customto return to ambient temperature
filtrationthe insoluble matter is filtered off
customthe filtrate evaporated under reduced pressure
customThe crude residue obtained
filtrationThe precipitate is filtered off
washwashed twice with 30 ml of ether
customdried in vacuo

Sources & evidence

ORD record: ord-a0ca9781b9f748748db783770eff37c7
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04696942

Reaction notes

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