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

HRID 517880노트

반응식

HRID 517880 반응식
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

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 887MethanolHCID 14798Sodium Hydroxide2회HCID 89690447Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ecdfc944bf5c4f659b526ec669676546
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115129B2

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