Lithium Hydroxide → HCID 57448192, compound

HRID 1438182Notes

Reaction equation

HRID 1438182 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:26]=3[F:35])[C:21]([O:23]C)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1.[Li+].[OH-]>C1COCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH:20]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:26]=3[F:35])[C:21]([OH:23])=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 57448190HCID 57448190, compound

Product 1

HCID 57448192HCID 57448192, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

139C (80 mg, 0.21 mmol) was dissolved in THF (2 mL). 1M LiOH (0.4 mL) was added, and the reaction was stirred at rt for 0.5 h. Additional 1M LiOH was added (0.4 mL) and the reaction was stirred for 3 h. The solvent was removed under reduced pressure, and water (10 mL) was added. The solution was acidified with 1 N HCl, then purified via preparative HPLC (MeOH/water/TFA) to provide 139D (65 mg, 64%). LC-MS: 373.18 (M+H)+.

Workup

  1. stirringthe reaction was stirred for 3 h
  2. customThe solvent was removed under reduced pressure, and water (10 mL)
  3. additionwas added
  4. custompurified via preparative HPLC (MeOH/water/TFA)

Sources & evidence

ORD record
ord-3cd6429f291c4961b7289c0895636175
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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