Dicyclohexylcarbodiimide → 2-Nitrobenzyl 11-mercaptoundecanoate

HRID 657463

反応式

HRID 657463 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[SH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[SH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[O:24]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 119232-Nitrobenzyl alcoholHCID 54350211-Mercaptoundecanoic Acid

生成物 1

HCID 578526732-Nitrobenzyl 11-mercaptoundecanoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

One equivalent of 2-nitrobenzyl alcohol (2.17 g, 14.15 mmol) was combined with one equivalent of 11-mercaptoundecanoic acid (3.09 g, 14.15 mmol), 0.1 equivalents DMAP (0.173 g, 1.42 mmol) and dissolved in 50 mL CH2Cl2. To this mixture a solution of DCC (2.92 g, 14.15 mmol) in 30 mL CH2Cl2 was slowly added while stirring. Upon addition a white precipitate formed after a few minutes. The mixture was stirred at room temperature overnight. Vacuum filtration removed the white precipitate and the filtrate was concentrated by rotovap. Silica gel column chromatography was employed for purification using C1H2Cl2/MeOH (v/v 50:1) as the eluent. The product was dried over Na2SO4, the solvent removed by rotovap, and dried under vacuum thus producing a yellow solid. Yield: 3.57 g (71.4%). 1H-NMR (CDCl3) δ (ppm): 8.1 (d, 1H, Ar), 7.6 (t, 1H, Ar), 7.5 (d, 1H, Ar), 7.4 (t, 1H, Ar), 5.5 (s, 2H, O—CH2), 2.6 (t, 1H, SH) 2.5 (q, 2H, CH2—SH), 2.4 (t, 2H, CH2—C═O), 1.6 (m, 4H, CH2), 1.2 (m, 12H, CH2). 13C-NMR (CDCl3) δ (ppm): 173.5, 147.0, 134.1, 132.7, 129.5, 129.2, 125.5, 63.2, 34.6, 34.4, 29.8, 29.7, 29.6, 29.5, 29.4, 28.8, 25.3, 25.1. MS (ESI): (M+Na)+=376.19 (calc. 376.47).

後処理

  1. additionUpon addition a white precipitate
  2. customformed after a few minutes
  3. stirringThe mixture was stirred at room temperature overnight
  4. filtrationVacuum filtration
  5. customremoved the white precipitate
  6. concentrationthe filtrate was concentrated by rotovap
  7. customSilica gel column chromatography was employed for purification
  8. dry with materialThe product was dried over Na2SO4
  9. customthe solvent removed by rotovap
  10. customdried under vacuum
  11. customthus producing a yellow solid

出典と根拠

ORDレコード
ord-9fbcf8ff33924464a5ffacfeab03771e
出典データセット
uspto-grants-2011_12
特許番号
US08076125B2

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