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Dicyclohexylcarbodiimide → 3-Benzyloxy-1-(succinimidooxycarbonylmethyl)-pyrid-2-one

HRID 1381170
ノート
印刷プレビュー

反応式

HRID 1381170 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH2:15][C:16]([O:18][N:21]2[C:25](=[O:26])[CH2:24][CH2:23][C:22]2=[O:27])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 133367273-Benzyloxy-1-carboxymethylpyrid2-one

生成物 1

HCID 133367283-Benzyloxy-1-(succinimidooxycarbonylmethyl)-pyrid-2-one収率 82.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

3-Benzyloxy-1-carboxymethylpyrid-2-one (2 g) is dissolved in dimethylformamide (DMF) (25 ml) and to this solution is added N-hydroxysuccinimide (1 g). The resultant solution is cooled and to it is added dicyclohexylcarbodiimide (DCCI) (11.8 g) in DMF (5 ml). The mixture is allowed to stand overnight to give a brown supernatant and a white precipitate. The precipitate is filtered off, washed with a little DMF and then evaporated to dryness under high vacuum. The crude product is dissolved in a minimum volume of dichloromethane and diethyl ether is added to this solution until it becomes cloudy. The solution is then cooled and the resultant precipitate is filtered off and washed with a little diethyl ether to give 3-benzyloxy-1-(succinimido-oxycarbonylmethyl)-pyrid-2-one (2.26 g, 82%), m.p. 187°-188° C.

後処理

  1. customto give a brown supernatant
  2. filtrationThe precipitate is filtered off
  3. washwashed with a little DMF
  4. customevaporated to dryness under high vacuum
  5. dissolutionThe crude product is dissolved in a minimum volume of dichloromethane and diethyl ether
  6. additionis added to this solution until it
  7. temperatureThe solution is then cooled
  8. filtrationthe resultant precipitate is filtered off
  9. washwashed with a little diethyl ether

出典と根拠

ORDレコード
ord-102e7c27b63b44e5866bee463f762825
出典データセット
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04585780

反応ノート

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