Lithium Hydroxide → HCID 67195816, compound

HRID 2366864Notes

Reaction equation

HRID 2366864 reaction equation
[OH-].[Li+].[C:3]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([O:18]CCCC)=[O:17])=[CH:13][CH:14]=2)[C@H:9]([NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:8][C@@H:7]1[CH3:30])(=[O:5])[CH3:4]>O.C(O)C>[C:3]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=2)[C@H:9]([NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:8][C@@H:7]1[CH3:30])(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67195717HCID 67195717, compound

Product 1

HCID 67195816HCID 67195816, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (0.365 g, 15.23 mmol) in water (5 mL) was added to a solution of butyl (2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinecarboxylate (for a preparation, see Intermediate 65) (1.982 g, 5.08 mmol) in ethanol (5 ml) and the mixture was stirred for 16 h at this temperature then concentrated in vacuo. The aqueous residue was diluted with water (5 mL) and the aqueous phase was washed with Et2O (10 mL). The aqueous layer was acidified with a 2M HCl aqueous solution (pH<2) and extracted with EtOAc (2×10 mL). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give (2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinecarboxylic acid (1.45 g, 4.34 mmol, 85% yield) as a colourless crystalline solid

Workup

  1. customfor a preparation
  2. concentrationthen concentrated in vacuo
  3. additionThe aqueous residue was diluted with water (5 mL)
  4. washthe aqueous phase was washed with Et2O (10 mL)
  5. extractionextracted with EtOAc (2×10 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8319666ce3f422e9fa2545e574df260
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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