Methanol → HCID 59205325, compound

HRID 2242649Notes

Reaction equation

HRID 2242649 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([N:27]1[CH2:31][CH2:30][C@H:29]([F:32])[CH2:28]1)=[O:26])[C@H:10]([CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]CCCC)=[O:19])[CH2:14][CH2:13]1)[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Li+].S(=O)(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([N:27]1[CH2:31][CH2:30][C@H:29]([F:32])[CH2:28]1)=[O:26])[C@H:10]([CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)[CH3:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 68430640HCID 68430640, compound

Product 1

HCID 59205325HCID 59205325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the material prepared in Step B (3.0 g, 6.1 mmol) in THF (30 mL) was added methanol (10 mL) followed by 1N aqueous lithium hydroxide (30 mL). After 24 h at ambient temperature the mixture was brought to pH 1 with 1N aqueous sodium bisulfate. The mixture was extracted with 100 mL of ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo, affording the title compound. This was used without further purification. LC/MS 406.2 (M+1).

Workup

  1. extractionThe mixture was extracted with 100 mL of ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-820882eeaa554c22a27ac532b7d5efbe
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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