Tetrabutylammonium Fluoride → HCID 58504042, compound

HRID 2407725Notes

Reaction equation

HRID 2407725 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][C@H:11]([CH3:21])[CH2:12][O:13][Si](C(C)(C)C)(C)C)[N:5]=[C:4]([C:22]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[S:37][C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=4)=[N:35][CH:34]=3)[CH2:28][CH2:27]2)=[O:23])[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][C@H:11]([CH3:21])[CH2:12][OH:13])[N:5]=[C:4]([C:22]([NH:24][CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][C:33]3[S:37][C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=4)=[N:35][CH:34]=3)[CH2:30][CH2:31]2)=[O:23])[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66989776HCID 66989776, compound

Product 1

HCID 58504042HCID 58504042, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound prepared in Example 209 (0.032 g) was suspended in tetrahydrofuran (10 mL) and aqueous tetrabutylammonium fluoride solution (1 mol/L; 0.103 mL) added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by preparative TLC, (eluant: 10% (9:1 methanol/concentrated ammonium hydroxide)/ethyl acetate) to furnish the title compound (0.020 g) having the following physical properties.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude material, which
  7. customwas purified by preparative TLC, (eluant: 10% (9:1 methanol/concentrated ammonium hydroxide)/ethyl acetate)

Sources & evidence

ORD record
ord-fcdd6e40c558437eb0b2501c61ba9265
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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