Lithium Hydroxide → HCID 59536933, compound

HRID 709122Notes

Reaction equation

HRID 709122 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([O:24]C)=[O:23])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:16])[F:17])[C:11](=[O:20])[N:10]([CH2:21][C:22]([OH:24])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59536841HCID 59536841, compound

Product 1

HCID 59536933HCID 59536933, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The enantiomerically pure compound of Example 6A (1.6 g, 4.21 mmol) was dissolved in 77 ml of methanol, and 17 ml of a 1M solution of lithium hydroxide in water were added. The mixture was stirred at RT for 1 h and then concentrated on a rotary evaporator. The residue was diluted with 100 ml of water and acidified to pH 1-2 with 1 N hydrochloric acid. The precipitated product was filtered off, washed successively with water and cyclohexane and sucked dry. Further drying under high vacuum gave 1.1 g (71% of theory) of the title compound.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. additionThe residue was diluted with 100 ml of water
  3. filtrationThe precipitated product was filtered off
  4. washwashed successively with water and cyclohexane
  5. customsucked dry
  6. customFurther drying under high vacuum

Sources & evidence

ORD record
ord-44b9726ef1c541929a9f4072f369eb21
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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