Acetic Acid → 6-(2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

HRID 1435166

反応式

HRID 1435166 の反応式
C([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])([CH3:16])[CH:4]1[CH3:25])C.Br.C(O)(=O)C.C(OC(OCC)C=C)C>C(O)C>[CH3:25][C:4]1[C:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])([CH3:16])[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([OH:15])(=[O:14])=[O:13])[CH:7]=2)[N:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 624773,3-Diethoxy-1-propeneHCID 866035256-(1-ethyl-2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

生成物 1

HCID 598554226-(2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

6-(2,3-Dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid was synthesised as described in Example 5. To a stirred solution of 6-(1-ethyl-2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid (1.8 g, 5.3 mmol) in ethanol (200 ml) at ambient temperature was added hydrobromic acid (10 ml 48% aqueous solution). After 1 Hr the reaction solvent was removed in vacuo. The hydrobromide salt was re-dissolved in acetonitrile (150 ml) and acetic acid (1.54 ml) and acrolein diethyl acetal (6.6 g, 51 mmol). The reaction mixture was heated to 70° C. for 30 minutes. The solution was cooled and the solvent removed in vacuum. The product was rapidly purified by preparative HPLC on reverse phase C18 column using gradient elution of water containing 10% acetonitrile to acetonitrile (containing 0.1% TFA) as solvent over 30 minutes. All fractions were monitored by MALDI-TOF mass spectrometry (M/Z=498). Fractions containing product mass were pooled. Evaporation of the solvent gave a sticky mass (162 mg 11%). It was immediately used for the next reaction.

後処理

  1. customAfter 1 Hr the reaction solvent was removed in vacuo
  2. dissolutionThe hydrobromide salt was re-dissolved in acetonitrile (150 ml)
  3. temperatureThe solution was cooled
  4. customthe solvent removed in vacuum
  5. customThe product was rapidly purified by preparative HPLC on reverse phase C18 column
  6. washelution of water containing 10% acetonitrile to acetonitrile (containing 0.1% TFA) as solvent over 30 minutes
  7. additionFractions containing product mass
  8. customEvaporation of the solvent
  9. customgave a sticky mass (162 mg 11%)
  10. customIt was immediately used for the next reaction

出典と根拠

ORDレコード
ord-bb92fb706dbd4e6897373364459a2617
出典データセット
uspto-grants-2009_11
特許番号
US07615646B2

関連ノート

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