Benzoyl chloride → N-Benzoyl-L-asparagine

HRID 1489772

반응식

HRID 1489772 반응식
O.[NH2:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6].C(=O)([O-])[O-].[K+].[K+].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:17]([NH:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][C:5](=[O:7])[NH2:6])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 170358L-Asparagine, monohydrate

생성물 1

HCID 7062826N-Benzoyl-L-asparagine수율 68.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a vigorously stirred solution of 2 g (0.013 mol) of L-asparagine monohydrate and 2.02 g (0.014 mol) of potassium carbonate in 15 ml of water, 1.51 ml (0.013 mol) of benzoyl chloride was added dropwise, over a period of 15 min., at room temperature. The stirring was continued for 2 hour, then the mixture was extracted with 10 ml of ether and the aqueous phase was acidified to pH 2 with concentrated hydrochloric acid. The white precipitate was filtered off, washed with water and purified by crystallization from isopropyl alcohol to give 2.1 g (68% yield) of the title compound at 190°-192° C.; NMR (DMSO-d6): 2.62 (m, 2H, CH2); 3.32 (broad s, 1H, OH); 4.72 (m, 1H, CH); 6.64-8.0(m. 7H, aromatic, NH2); 8.6 (d, 1H, NH).

후처리

  1. extractionthe mixture was extracted with 10 ml of ether
  2. filtrationThe white precipitate was filtered off
  3. washwashed with water
  4. custompurified by crystallization from isopropyl alcohol

출처 및 근거

ORD 기록
ord-2838a3882e9445b4b234d3469e829e23
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679688

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