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Cyanamide → N-cyano-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide

HRID 987229
ノート
印刷プレビュー

反応式

HRID 987229 の反応式
C1CCC([N:7]=[C:8]=[N:9]C2CCCCC2)CC1.ON1C(=O)CCC1=O.[CH2:24]([O:26][CH:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:43][CH:42]=2)=[CH:34][CH:33]=1)[C:28](O)=[O:29])[CH3:25].C(N(C(C)C)CC)(C)C.N#CN>C(#N)C.C(O)(=O)C>[C:8]([NH:9][C:28](=[O:29])[CH:27]([O:26][CH2:24][CH3:25])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][S:48]([CH3:51])(=[O:50])=[O:49])=[CH:43][CH:42]=2)=[CH:34][CH:33]=1)#[N:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 9864CyanamideHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 113387772-Ethoxy-3-[4-(2-{4-[(methanesulfonyl)oxy]phenyl}ethoxy)phenyl]propanoic acid

生成物 1

HCID 9954507N-cyano-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide
収率 89.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

DCC (0.444 g; 2.15 mmole) and N-hydroxy-succinimide (0.247 g; 2.15 mmole) were added to a solution of 2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid (described in Example 2) (0.8 g; 1.96 mmole) in acetonitrile (20 ml) at 0° C. After stirring at room temperature overnight a precipitate was filtered off and diisopropylethylamine (1 ml; 5.88 mmole) and cyanamide (0.165 g; 3.92 mmole) were added. After stirring overnight the reaction mixture was poured onto potassium hydrogen sulfate (1M, 20 ml) and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried (sodium sulfate) and the solvent was evaporated. Chromatography of the crude product on silica gel using ethyl acetate:heptane; acetic acid (10:10:1) as eluant gave 0.755 g (yield 89%) of N-cyano-2-ethoxy-3-[4-(2-{4-methanesulfonyloxy-phenyl}ethoxy)phenyl]propanoic amide.

後処理

  1. filtrationwas filtered off
  2. stirringAfter stirring overnight the reaction mixture
  3. additionwas poured onto potassium hydrogen sulfate (1M, 20 ml)
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-79b38f62000547478ed8201460de3a1e
出典データセット
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06630600B1

反応ノート

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