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 2366947Notes

Reaction equation

HRID 2366947 reaction equation
[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]

Participants

4

Reactant 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

Product 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 acidYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e1d157af5b744e248323bebf4223f214
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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