Water → HCID 57516944, compound

HRID 1944878Notes

Reaction equation

HRID 1944878 reaction equation
FC(F)(F)[C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:9][CH:8]=1)C)=O.C([O-])([O-])=O.[K+].[K+].O>CO>[CH3:3][NH:5][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57516936HCID 57516936, compound

Product 1

HCID 57516944HCID 57516944, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 36 (0.221 g, 0.7752 mmol) was reacted with K2CO3 (0.7752 mmol, 0.107 g) in 12 mL of 2:1 MeOH:Water at room temperature overnight. The reaction was worked up quenching the reaction with 1× saturated NaHCO3, extracted 4×25 ml EtOAc then washed 1× water, 1× saturated NaCl, dried over Na2SO4, then concentrated. The product was purified 0-10% MeOH in DCM over 15 min on TEA silica 12 g. ES/MS calcd. for C12H15NO 189.1. Found m/z=190 (M+H)+.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction was worked up quenching
  4. customthe reaction with 1× saturated NaHCO3
  5. extractionextracted 4×25 ml EtOAc
  6. washthen washed 1× water, 1× saturated NaCl
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe product was purified 0-10% MeOH in DCM over 15 min on TEA silica 12 g

Sources & evidence

ORD record
ord-c514b21679ed4a77b59f158ccb7527b3
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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