Lithium Hydroxide → HCID 67421148, compound

HRID 2237759Notes

Reaction equation

HRID 2237759 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:17][N:16]2[C:12](=[N:13][C:14]3[CH:21]=[C:20]([C:22]([O:24]C)=[O:23])[CH:19]=[CH:18][C:15]=32)[CH2:11][C@@H:10]1[C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=1[F:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:17][N:16]2[C:12](=[N:13][C:14]3[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][C:15]=32)[CH2:11][C@@H:10]1[C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=1[F:34])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67421212HCID 67421212, compound

Product 1

HCID 67421148HCID 67421148, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 380 mg (0.80 mmol) of the product from Step B in 7.5 mL of 2:1 THF/methanol was added 2.5 mL (2.5 mmol) of 1N aqueous lithium hydroxide solution. The reaction mixture was stirred at ambient temperature for 3 h, then the organic solvent removed in vacuo. The mixture was quenched with 50 mL of 1N aqueous hydrochloric acid, and extracted with 50 mL of ethyl acetate. The organic solution was next washed with 1N aqueous hydrochloric acid, once with saturated aqueous brine (50 mL each), dried over sodium sulfate, filtered and concentrated in vacuo. The crude solid was purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 0% to 80% acetonitrile/water with 0.1% TFA) to afford the title compound as a white foam. LC/MS 462.4 (M+1).

Workup

  1. customthe organic solvent removed in vacuo
  2. customThe mixture was quenched with 50 mL of 1N aqueous hydrochloric acid
  3. extractionextracted with 50 mL of ethyl acetate
  4. washnext washed with 1N aqueous hydrochloric acid, once with saturated aqueous brine (50 mL each)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude solid was purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 0% to 80% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-354b49e330de4dc7925ec94636af946a
Source dataset
uspto-grants-2010_05
Patent number
US07718667B2

Reaction notes

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