Lithium hydroxide, monohydrate → HCID 59626018, compound

HRID 403299Notes

Reaction equation

HRID 403299 reaction equation
[F:1][C:2]([F:23])([F:22])[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)[NH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.O[Li].O>C1COCC1.O>[F:22][C:2]([F:1])([F:23])[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)[NH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59626078HCID 59626078, compound

Product 1

HCID 59626018HCID 59626018, compoundYield 94%

Reagents, catalysts & solvents 1

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

Procedure

A solution of compound 15d (TFA salt, 500 mg, 1.15 mmol), and LiOH.H2O (132.7 mg, 3.16 mmol) in THF/H2O (10 mL/10 mL) was stirred at 45° C. overnight. 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 15e (330 mg), which was used in the next reaction without further purification. MS m/z (M+H+) 306.0.

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-a591432874bf4b60946ca0383192fc89
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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