Aniline → N-p-methylphenylsulfonyl-L-proline anilide

HRID 1855924ノート

反応式

HRID 1855924 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:18][CH2:17][CH2:16][C@H:12]2[C:13](O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.C1(N=C=NC2CCCCC2)CCCCC1.N[C:42]1C=CC=CC=1.[C:48](OCC)(=[O:50])C>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:48](=[O:50])[C@@H:24]2[CH2:25][CH2:23][CH2:22][NH:21]2)[C:18]2[CH:17]=[CH:16][CH:12]=[CH:13][CH:42]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 5

HCID 6115AnilineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 691957(2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

生成物 1

HCID 131711845N-p-methylphenylsulfonyl-L-proline anilide収率 47.5%

実験手順

In this example, 8.07 g of N-p-methylphenylsulfonyl-L-proline and 3.03 g of triethylamine are dissolved in 100 ml ethyl acetate, and then dicyclohexyl carbodiimide (DCC; 6.18 g) is added thereto under ice cooling (5°-10° C.). The mixture is stirred for 20 minutes. After addition of 2.79 g aniline, the mixture is subjected to reaction at room temperature overnight with stirring. The deposited precipitate is filtered off, and the filtrate is washed three times with 100 ml water, twice with 100 ml 1N HCl, and then three times with 100 ml water. After drying over anhydrous sodium sulfate (about 30 g), the filtrate is concentrated under reduced pressure, and recrystallized from ethyl acetate-n-hexane (2:1 by volume), whereby N-p-methylphenylsulfonyl-L-proline anilide (compound number 18; 4.9 g; m.p. 140° C.) is obtained. Yield: 47.5%.

後処理

  1. customunder ice cooling (5°-10° C.)
  2. customthe mixture is subjected to reaction at room temperature overnight
  3. stirringwith stirring
  4. filtrationThe deposited precipitate is filtered off
  5. washthe filtrate is washed three times with 100 ml water
  6. dry with materialAfter drying over anhydrous sodium sulfate (about 30 g)
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customrecrystallized from ethyl acetate-n-hexane (2:1 by volume)

出典と根拠

ORDレコード
ord-df35b6028ee04179be4a8269b53095d9
出典データセット
uspto-grants-1980_08
特許番号
US04217130

反応ノート

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