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

HRID 1871789
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HRID 1871789 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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-(succinimidooxycarbonylmethyl)-pyrid-2-one (2.26 g, 82%), m.p. 187°-188° C.

후처리

  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

출처 및 근거

ORD 기록
ord-aceeb0ae69f34512bfbef2da42a4d82c
출처 데이터셋
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE036831

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