Lithium Hydroxide → 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylic acid

HRID 2366947노트

반응식

HRID 2366947 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([C:19]([O:21]CC)=[O:20])[N:16]=[CH:15]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-].[Li+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[N:16]=[CH:15]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]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 68162205ethyl 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylate

생성물 1

HCID 529343341-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylic acid수율 65%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of ethyl 1-[(cis)1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylate (for a preparation see Intermediate 82) (1.8 g, 4.2 mmol), methanol (15 mL), and lithium hydroxide (1M in water, 15 mL) was stirred at room temperature for 6 h then most of the methanol was removed in vacuo. The residue was diluted with water (15 mL) and acidified with glacial acetic acid. The resulting aqueous phase was extracted with AcOEt (3×30 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo to give 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylic acid (1.1 g, 2.75 mmol, 65%) as a colourless solid.

후처리

  1. custommost of the methanol was removed in vacuo
  2. additionThe residue was diluted with water (15 mL)
  3. extractionThe resulting aqueous phase was extracted with AcOEt (3×30 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e1d157af5b744e248323bebf4223f214
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697725B2

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