Tetrabutylammonium Fluoride → HCID 22242789, compound

HRID 891599Notes

Reaction equation

HRID 891599 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][S:33][CH2:32][CH2:31]3)=[O:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[S:33]1[CH2:34][CH2:35][N:30]([C:28]([C:26]2[N:27]=[C:23]([N:21]3[CH2:22][CH:19]([OH:18])[CH2:20]3)[S:24][CH:25]=2)=[O:29])[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242814HCID 22242814, compound

Product 1

HCID 22242789HCID 22242789, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-thiomorpholinocarbonyl-1,3-thiazol-2-yl)azetidine (1.16 g, 2.10 mmol) (obtained as described in Reference Example 25(1)) in anhydrous tetrahydrofuran (35 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (2.52 ml, 2.52 mmol), and the reaction mixture was stirred for 30 minutes. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 1-(4-thiomorpholinocarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (599 mg, yield 100%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-705a192d7cd648ee829cfdb962699bb6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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