Lithium hydroxide, monohydrate → HCID 59625707, compound

HRID 403301Notes

Reaction equation

HRID 403301 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20]C)=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:22])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.O[Li].O>C1COCC1.O>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:22])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67287768HCID 67287768, compound

Product 1

HCID 59625707HCID 59625707, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of compound 15f (264 mg, 0.93 mmol), and LiOH.H2O (156.4 mg, 3.73 mmol) in THF/H2O (10 mL/10 mL) was stirred at 45° C. for 5 h. The resulting mixture was concentrated and diluted with water. The aqueous layer was acidified with 1N aqueous HCl to pH˜4 and extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated to give compound 15g (252 mg), which was used in the next reaction without further purification. MS m/z (M+H+) 270.1.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d94dbfcbae574cc1982f79f07f26f61d
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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