Potassium Hydroxide → HCID 21093760, compound

HRID 1350046Notes

Reaction equation

HRID 1350046 reaction equation
[Cl:1][C:2]1[C:7]([NH:8]C(=O)C(C)(C)C)=[C:6]([C:15]2(O)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([O:22][CH3:23])=[CH:4][CH:3]=1.[OH-].[K+]>O>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([C:15]2[CH2:20][CH2:19][O:18][CH2:17][CH:16]=2)[C:5]([O:22][CH3:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21093763HCID 21093763, compound

Product 1

HCID 21093760HCID 21093760, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of intermediate 13 (0.365 g, 1.06 mmol) and potassium hydroxide (0.24 g, 4.27 mmol) in glycol (0.5 mL) was stirred at 100° C. overnight. The reaction mixture was poured into water and extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (eluent: cyclohexane/EtOAc:90/10) to give title compound (0.187 g, 73%) as a white solid.

Workup

  1. extractionextracted three times with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography (eluent: cyclohexane/EtOAc:90/10)

Sources & evidence

ORD record
ord-51f880fddb64438aabb5422f9fdaaa0c
Source dataset
uspto-grants-2007_05
Patent number
US07214676B2

Reaction notes

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