Potassium Hydroxide → Levetiracetam

HRID 2309726노트

반응식

HRID 2309726 반응식
[NH2:1][C:2]([C@@H:4]([NH:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11]Cl)[CH2:5][CH3:6])=[O:3].[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:5]([C@H:4]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:13])[C:2]([NH2:1])=[O:3])[CH3:6]

참가 물질

5

반응물 2

HCID 14797Potassium Hydroxide2회HCID 29938341N-(1-Amino-1-oxobutan-2-yl)-4-chlorobutanamide, (S)-

생성물 1

HCID 5284583Levetiracetam수율 60.7%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

6.2 g (0.03 mole) of (S)-N-[1-(aminocarbonyl)propyl]-4-chlorobutanamide and 0.484 g (0.0015 mole) of tetrabutylammonium bromide are mixed in 45 ml of dichloromethane at 0° C. under a nitrogen atmosphere. 2.02 g (0.036 mole) of potassium hydroxide powder are added over 30 minutes, at such a rate that the temperature of the reaction mixture does not exceed +2° C. The mixture is then stirred for one hour, after which a further 0.1 g (0.0018 mole) of ground potassium hydroxide is added and stirring continued for 30 minutes at 0° C. The mixture is allowed to return to ambient temperature. The insoluble matter is filtered off and the filtrate is concentrated under reduced pressure. The residue obtained is recrystallized from 40 ml of ethyl acetate in the presence of 1.9 g of 0,4 nm molecular sieve. The latter is removed by hot filtration to give 3.10 g of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide.

후처리

  1. customdoes not exceed +2° C
  2. stirringstirring
  3. waitcontinued for 30 minutes at 0° C
  4. customto return to ambient temperature
  5. filtrationThe insoluble matter is filtered off
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue obtained
  8. customis recrystallized from 40 ml of ethyl acetate in the presence of 1.9 g of 0,4 nm molecular sieve
  9. customThe latter is removed by hot filtration

출처 및 근거

ORD 기록
ord-c304cbe51d5e47e3b89ee22a16f3c802
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04696943

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