Benzoyl chloride → N-Benzoyl-L-asparagine

HRID 1489772ノート

反応式

HRID 1489772 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 7062826N-Benzoyl-L-asparagine収率 68.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2838a3882e9445b4b234d3469e829e23
出典データセット
uspto-grants-1997_10
特許番号
US05679688

反応ノート

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