Methanol → HCID 10176913, compound

HRID 2099169Notes

Reaction equation

HRID 2099169 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([N:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[C:13]=3[C:12]([C:25]#[C:26][Si](CC)(CC)CC)=[CH:11]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.[OH-].[K+]>C1COCC1>[C:25]([C:12]1[C:13]2[C:18]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:17][CH:16]=[N:15][C:14]=2[NH:10][CH:11]=1)#[CH:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 22484560HCID 22484560, compound

Product 1

HCID 10176913HCID 10176913, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the product from Method S (194 mg/0.40 mmol) dissolved in 2.0 mL of dry THF was added dropwise 0.4 mL (0.4 mmol) of a 1 M solution of tetrabutylammonium fluoride in THF. The resulting mixture stirred at room temperature for 10 minutes, then was transferred to a methanol solution (3.0 mL) containing 1 gram of KOH, the new mixture stirred at room temperature for 15 minutes and concentrated in vacuo. The residue was partitioned between water and ethyl acetate, the ethyl acetate layer washed with water and brine, dried over MgSO4 and concentrated to dryness in vacuo. The crude product was purified by silica-gel chromatography (2:1 ethyl acetate/hexanes) affording 72 mg (64%) of the title compound as a white crystalline solid. Mp 179-181° C. 1H NMR (400 MHz) (CDCl3) d: 1.72 (br s, 6H), 3.20 (s, 1H), 3.82-3.83 (m, 4H), 7.47 (s, 1H), 8.35 (s, 1H). LRMS: 227 (M+1).

Workup

  1. stirringthe new mixture stirred at room temperature for 15 minutes
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. washthe ethyl acetate layer washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crude product was purified by silica-gel chromatography (2:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1be01c248e3b41e38e16d8fb94d6ff7f
Source dataset
uspto-grants-2009_08
Patent number
US07569569B2

Reaction notes

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