Tetrahydrofuran → HCID 59750418, compound

HRID 748396Notes

Reaction equation

HRID 748396 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC[Si](C)(C)C)=[O:23])[CH:15]=[CH:14][CH:13]=2)=[N:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>CN(C)C=O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 22939487HCID 22939487, compound

Product 1

HCID 59750418HCID 59750418, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Trimethylsilyl)ethyl 5-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]valerate (0.23 g, 0.52 mmol) was dissolved in N,N-dimethylformamide (2 ml), and 1.0 M tetrabutylammonium fluoride in tetrahydrofuran (1.3 ml, 1.3 mmol) was added thereto. The reaction mixture was stirred for 15 minutes and concentrated under reduced pressure. Trifluoroacetic acid (2.5 ml) was added to the residue, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was subjected to a silica gel (25 g) column chromatography. The fractions eluted with hexane-ethyl acetate (3:1, v/v) were collected and concentrated. The residue was recrystallized from ethanol-acetone to give the titled compound (0.10 g, 55%) as white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTrifluoroacetic acid (2.5 ml) was added to the residue
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. washThe fractions eluted with hexane-ethyl acetate (3:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol-acetone

Sources & evidence

ORD record
ord-5b9b4bf1edd148bd8f497ed6b05668ba
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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