Dicyclohexylcarbodiimide → 5-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl ester

HRID 1263603

反応式

HRID 1263603 の反応式
[CH2:1]([O:4][C:5](=[O:18])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([OH:11])=[O:10])[CH:2]=[CH2:3].O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:1]([O:4][C:5](=[O:18])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([O:11][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26])=[O:10])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 206558603-Allyloxycarbonyl-5-nitrobenzoic acid

生成物 1

HCID 229860995-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl ester収率 54.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 7(a) (10.00 g), N-hydroxysuccinimide (5.04 g) and DCCI (9.03 g) in dichloromethane(400 ml) was stirred at ambient temperature for 3.5 h. The white precipitate which formed was filtered off and the filtrate evaporated under reduced pressure to give a yellow oil. This was purified by flash chromatography eluting with ethyl acetate/hexane (75:25) to give 5-nitro-isophthalic acid 1-(2.5-dioxo-pyrrolidin-1-yl) ester 3-allyl ester (7(b)) as a yellow solid (7.58 g).

後処理

  1. customThe white precipitate which formed
  2. filtrationwas filtered off
  3. customthe filtrate evaporated under reduced pressure
  4. customto give a yellow oil
  5. customThis was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (75:25)

出典と根拠

ORDレコード
ord-8455f08f6a464fa2906666ce7887a45f
出典データセット
uspto-grants-2003_04
特許番号
US06541491B1

関連ノート

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