Water → ethyl (2RS)-2-acetylamino-3-(3-cyanophenyl)propanoate

HRID 47728

반응식

HRID 47728 반응식
[C:1]([NH:4][C:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=1)(C([O-])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[I-].[Li+].CN(C)C=O.O>C(OCC)(=O)C.C1CCCCC1>[C:1]([NH:4][CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 66321Lithium iodideHCID 22747914Ethyl 2-acetylamino-2-(3-cyanobenzyl)malonate

생성물 1

HCID 85797672ethyl (2RS)-2-acetylamino-3-(3-cyanophenyl)propanoate

시약·촉매·용매 1

HCID 21867204Cyclohexane ethylacetate용매

반응 조건

온도
150 °C

실험 절차

The process is performed as in Example 5, starting with 14.9 g of ethyl 2-acetylamino-2-(3-cyanobenzyl)malonate, 30 g of anhydrous lithium iodide and 150 cm3 of dry dimethylformamide. After stirring for 5 hours at a temperature in the region of 150° C., the reaction mass is cooled to room temperature. 1500 cm3 of water are added and the mixture is extracted with 3 times 300 cm of ethyl acetate. The extracts are combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 45° C. After drying in an oven at a temperature in the region of 40° C. under reduced pressure (10 Pa), 11.39 g of ethyl (2RS)-2-acetylamino-3-(3-cyanophenyl)propanoate are obtained in the form of a beige-colored paste. (Rf=0.51 in a 90/10 by volume mixture of ethyl acetate/cyclohexane, on a Merck 60F254R silica plate).

후처리

  1. temperaturethe reaction mass is cooled to room temperature
  2. extractionthe mixture is extracted with 3 times 300 cm of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 45° C
  6. dry with materialAfter drying in an oven at a temperature in the region of 40° C. under reduced pressure (10 Pa), 11.39 g of ethyl (2RS)-2-acetylamino-3-(3-cyanophenyl)propanoate
  7. customare obtained in the form of a beige-colored paste

출처 및 근거

ORD 기록
ord-d79adc6f76f347a3a7b2f752585c18da
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699895B2

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