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

HRID 379267ノート

反応式

HRID 379267 の反応式
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]

参加物

11

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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 filrate 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.

後処理

  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)

出典と根拠

ORDレコード
ord-8f3d0fa0e63846b29ceec61b69174f0d
出典データセット
uspto-grants-2001_10
特許番号
US06297249B1

反応ノート

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