Tetrabutylammonium Fluoride → HCID 67524575, compound

HRID 993029Notes

Reaction equation

HRID 993029 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[NH:5][C:6](=[O:19])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:20][OH:21])[NH:5][C:6](=[O:19])[C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22890397HCID 22890397, compound

Product 1

HCID 67524575HCID 67524575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

O-tert-Butyldimethylsilyl-N-(3,4,5-trimethoxy-benzoyl)-L-serine methyl ester (15.91 g) was dissolved in THF (70 mL), and to the solution a THF solution (55.82 mL) of 1.0 M tetrabutylammonium fluoride was added at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude crystals were then recrystallized from methanol-ether-hexane to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude crystals were then recrystallized from methanol-ether-hexane

Sources & evidence

ORD record
ord-08f25d498b8247bb881f2fe63ca26d1b
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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