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

HRID 987229
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HRID 987229 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79b38f62000547478ed8201460de3a1e
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06630600B1

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