Sodium Hydroxide → {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetic acid

HRID 2366938ノート

反応式

HRID 2366938 の反応式
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:15]=[N:16][N:17]([CH2:19][C:20]([O:22]C)=[O:21])[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:15]=[N:16][N:17]([CH2:19][C:20]([OH:22])=[O:21])[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 68185402methyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetate

生成物 1

HCID 52933875{4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetic acid収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of methyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetate (for a preparation, see Intermediate 75) (250 mg, 0.582 mmol) in methanol (5 mL) was added a 2M NaOH aqueous solution (0.873 mL, 1.746 mmol). The reaction mixture was stirred at 50° C. for 1 hour, then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and a 2M NaOH aqueous solution. The layers were separated and the organic phase was further extracted with a 2M NaOH aqueous solution. The combined aqueous layers were acidified to pH=3 using a 2M HCl aqueous solution. then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over a Na2SO4 cartridge and concentrated in vacuo to give {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetic acid (245 mg, 0.566 mmol, 97%) as a white solid.

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between AcOEt
  4. customThe layers were separated
  5. extractionthe organic phase was further extracted with a 2M NaOH aqueous solution
  6. extractionthen extracted with EtOAc (3×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over a Na2SO4 cartridge
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-71ce38d56d4f4d25a6c73e7ff821b809
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

読み込み中…