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 2366938Notes

Reaction equation

HRID 2366938 reaction equation
[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]

Participants

4

Reactant 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

Product 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 acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-71ce38d56d4f4d25a6c73e7ff821b809
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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