Lithium Hydroxide → HCID 59536933, compound

HRID 574140Notes

Reaction equation

HRID 574140 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C@H:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:6]1.[OH-].[Li+]>CO.O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:7]2[N:8]([CH2:11][C@H:12]([OH:17])[C:13]([F:16])([F:14])[F:15])[C:9](=[O:10])[N:5]([CH2:4][C:3]([OH:25])=[O:2])[N:6]=2)=[CH:19][CH:20]=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 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 1N of hydrochloric acid. The precipitated product was filtered off, washed successively with water and cyclohexane and sucked dry. Further drying under HV gave the title compound (1.1 g, 71% of theory).

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 HV

Sources & evidence

ORD record
ord-d8cbf140453342cc9269a618a64e1efa
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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