Lithium hydroxide, monohydrate → HCID 90418912, compound

HRID 2202393Notes

Reaction equation

HRID 2202393 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=1)(=[O:12])=[O:11].O[Li].O>CCO.O>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90419005HCID 90419005, compound

Product 1

HCID 90418912HCID 90418912, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the compound 39E (350 mg, 1 mmol) in EtOH/H2O (10 mL/3 mL) was added LiOH.H2O (200 mg, 5 mmol) and the resulting suspension was stirred at 70° C. overnight. The solvent was concentrated and the residue was partitioned between aqueous 2 N HCl and EtOAc. The organic layer was separated and washed with water and brine, dried over Na2SO4 and concentrated to give the desired crude product 39F, which was confirmed by LCMS, and used in subsequent reaction without further purification. LC-MS: m/z 326.3 (M+H)+.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between aqueous 2 N HCl and EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c1f701b272546f1944d25bd53ac0496
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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