Lithium Hydroxide → HCID 59536933, compound

HRID 220629Notes

Reaction equation

HRID 220629 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, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The enantiomerically pure ester from Example 6A (1.6 g, 4.21 mmol) was dissolved in 77 ml of methanol and admixed with 17 ml of a 1M solution of lithium hydroxide in water. 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 a pH of 1-2 using 1N hydrochloric acid. The precipitated product was isolated by filtration, washed in succession with water and cyclohexane and sucked dry. After further drying in an HV, the title compound (1.1 g, 71% of theory) was obtained.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. additionThe residue was diluted with 100 ml of water
  3. customThe precipitated product was isolated by filtration
  4. washwashed in succession with water and cyclohexane
  5. customsucked dry
  6. customAfter further drying in an HV

Sources & evidence

ORD record
ord-8a987cdc5eb4404eb44abaaed129484e
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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