Hydrochloric Acid → 6-Oxo-(3-quinolin-3-yl)-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid

HRID 1837924노트

반응식

HRID 1837924 반응식
COP([CH2:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][NH:15][C:14]=2[N:13]=1)(=O)OC.[Li+].[Cl-].C([O:27][C:28](=[O:43])[CH2:29][CH:30]([C:33]1[CH:34]=[N:35][C:36]2[C:41]([CH:42]=1)=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=O)C.C1CCN2C(=NCCC2)CC1.[Li+].[OH-].Cl>C(#N)C.CCO.[Pd].O>[O:22]=[C:8]([CH2:9][CH2:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][NH:15][C:14]=2[N:13]=1)[CH2:7][CH2:31][CH:30]([C:33]1[CH:34]=[N:35][C:36]2[C:41]([CH:42]=1)=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29][C:28]([OH:43])=[O:27]

참가 물질

11

반응물 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 537991904-Oxo-3-(quinolin-3-yl)-butyric acid ethyl esterHCID 538016292-Oxo-5-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-pentyl-phosphonic acid dimethyl ester

생성물 1

HCID 101598546-Oxo-(3-quinolin-3-yl)-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Ketophosphonate 22-5 (1.0 g, 3.1 mmol), anhydrous LiCl (170 mg, 4.0 mmol), and 22-4 (0.797 g, 3.1 mmol) in anhydrous acetonitrile (60 mL), was treated with DBU (0.52 mL, 3.3 mmol) and the resulting suspension stirred at room temperature for 1 h. The solvent was removed at reduced pressure and the resulting residue partitioned between brine and methylene chloride. The organic layer was removed, dried, and concentrated to afford 22-6 as mixture of E and Z olefins. The crude mixture was dissolved in EtOH (50 mL), treated with 10% Pd/C (200 mg) and stirred under a hydrogen filled balloon for 4 h, then filtered. The filtrate was treated with LiOH (2.0 eq) and water (20 mL) and stirred at room temperature for 12 h, then neutralized with 1N HCl and evaporated Chromatography on silica gel (10% MeOH/methylene chloride) afforded 22-7 as a white solid.

후처리

  1. customThe solvent was removed at reduced pressure
  2. customthe resulting residue partitioned between brine and methylene chloride
  3. customThe organic layer was removed
  4. customdried
  5. concentrationconcentrated
  6. customto afford 22-6
  7. stirringstirred under a hydrogen filled balloon for 4 h
  8. filtrationfiltered
  9. stirringstirred at room temperature for 12 h
  10. customevaporated Chromatography on silica gel (10% MeOH/methylene chloride)

출처 및 근거

ORD 기록
ord-c91802f243b14779a591365d0d109df5
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784190B2

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