Lithium hydroxide, monohydrate → HCID 22271444, compound

HRID 1753072Notes

Reaction equation

HRID 1753072 reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]1[C:10]([O:19][CH3:20])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16]C)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:24]([O:23][C:21]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[C:10]([O:19][CH3:20])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([OH:16])=[O:15])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90093198HCID 90093198, compound

Product 1

HCID 22271444HCID 22271444, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the methyl 5-[bis(tert-butoxycarbonyl)amino]-6-methoxynicotinate (1 g, 2.61 mmol) in THF (10 mL) at 0° C. was added LiOH.H2O (275 mg, 6.54 mmol) in water (2.5 mL) and the reaction allowed to stir at room temperature for 4 hours. The reaction was diluted with water (5 mL) and extracted into DCM twice (2×10 mL). The aqueous layer was acidified to pH=5 with 10% citric acid solution and extracted into DCM (4×20 mL). The organic layers were collected, washed with brine (10 mL), dried over sodium sulphate and concentrated in vacuo to afford the title compound that was used directly in the next step.

Workup

  1. extractionextracted into DCM twice (2×10 mL)
  2. extractionextracted into DCM (4×20 mL)
  3. customThe organic layers were collected
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9315d1ef3d8543ad99e22deee18dd9a5
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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