Acetic Acid → HCID 22242781, compound

HRID 891574Notes

Reaction equation

HRID 891574 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:16][CH:17]=[C:18]([C:20](=[O:22])[NH2:21])[N:19]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:20]([C:18]1[N:19]=[C:15]([N:12]2[CH2:11][CH2:10][CH:9]([OH:8])[CH2:14][CH2:13]2)[S:16][CH:17]=1)(=[O:22])[NH2:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 22242974HCID 22242974, compound

Product 1

HCID 22242781HCID 22242781, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-t-butyidimethylsilyloxy-1-(4-carbamoyl-1,3-thiazol-2-yl)piperidine (1.226 g, 3.59 mmol) (obtained as described in Reference Example 15(1)) in anhydrous tetrahydrofuran (30 ml) were added acetic acid (1.85 ml) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (32.3 ml, 32.3 mmol) in an ice bath, and the mixture was stirred for 24 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column to afford 1-(4-carbamoyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (0.82 g, 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-785f00596fde43f0b909a142954f815a
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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