Lithium Hydroxide → HCID 86713396, compound

HRID 921277Notes

Reaction equation

HRID 921277 reaction equation
[C:1]([O:5][P:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:9]([O:8][P:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86713397HCID 86713397, compound

Product 1

HCID 86713396HCID 86713396, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 43B (0.635 g, 1.772 mmol) in THF (12.0 mL) and water (3.00 mL) was added lithium hydroxide (0.122 g, 2.14 mmol). The reaction mixture was stirred at room temperature for 2 hr and then the organics were removed under reduced pressure. The resulting mixture was diluted with 10 mL of pH 4 phosphate solution. The resulting mixture was extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated to afford Intermediate 43C (0.462 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.30 (br. s., 1H), 7.25 (d, J=8.4 Hz, 2H), 7.13-7.03 (m, 2H), 3.55 (s, 2H), 1.44 (s, 1H).

Workup

  1. customthe organics were removed under reduced pressure
  2. additionThe resulting mixture was diluted with 10 mL of pH 4 phosphate solution
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washThe combined EtOAc extracts were washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-94c5282079554af5a08e9291c6576c1e
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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