Hydrochloric Acid → 6-(2,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-6-yl)hexanoic acid

HRID 517880ノート

反応式

HRID 517880 の反応式
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:33](C(OC(C)(C)C)=O)[C:14]2=[N:15][C:16]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:18]=[C:13]2[CH2:12][CH2:11]1)C.[OH-].[Na+].CO.Cl>CCO.O>[C:22]1([CH3:25])[CH:21]=[CH:20][C:19]([C:17]2[N:18]=[C:13]3[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])[NH:33][C:14]3=[N:15][C:16]=2[C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 313Hydrochloric Acid2 回HCID 887MethanolHCID 14798Sodium Hydroxide2 回HCID 89690447Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

生成物 1

HCID 716574226-(2,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-6-yl)hexanoic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 4) (83 mg, 0.149 mmol) in EtOH (2 ml) was treated with 2M NaOH (0.223 ml, 0.446 mmol) and stirred at RT for 16 hours. MeOH (1 ml) and 2M HCl (0.372 ml, 0.744 mmol) were added and stirring continued at RT for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in water (30 ml). The mixture was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure. The crude product was dissolved in EtOH (1 ml) and treated with 2M NaOH (0.223 ml, 0.446 mmol). After stirring at RT overnight, the mixture was diluted with water (30 ml) and the pH was adjusted to pH1 using 1 M HCl. The aqueous portion was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure to afford an enantiomeric mixture.

後処理

  1. stirringstirring
  2. waitcontinued at RT for 16 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water (30 ml)
  5. extractionThe mixture was extracted with DCM (×3)
  6. concentrationthe combined organic extracts were concentrated under reduced pressure
  7. dissolutionThe crude product was dissolved in EtOH (1 ml)
  8. stirringAfter stirring at RT overnight
  9. extractionThe aqueous portion was extracted with DCM (×3)
  10. concentrationthe combined organic extracts were concentrated under reduced pressure
  11. customto afford an enantiomeric mixture

出典と根拠

ORDレコード
ord-ecdfc944bf5c4f659b526ec669676546
出典データセット
uspto-grants-2015_08
特許番号
US09115129B2

反応ノート

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