Tetrabutylammonium Fluoride → HCID 22243009, compound

HRID 891755Notes

Reaction equation

HRID 891755 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:36])[N:29]([CH2:33][CH2:34][OH:35])[CH:30]([CH3:32])[CH3:31])[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>[OH:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:36])[N:29]([CH2:33][CH2:34][OH:35])[CH:30]([CH3:31])[CH3:32])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242941HCID 22242941, compound

Product 1

HCID 22243009HCID 22243009, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[N-(2-hydroxyethyl)-N-isopropyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (2.49 g, 4.75 mmol) (obtained as described in Reference Example 59(1)) in anhydrous tetrahydrofuran (100 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (5.70 ml, 5.70 mmol) in an ice bath. The mixture was stirred in the ice bath for 1 hour. 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 using ethyl acetate:methanol (10:1) as the eluant to afford 3-hydroxy-1-{4-[N-(2-hydroxyethyl)-N-isopropyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (1.33 g, yield 98%) 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-93b7a7be32e742c78f30b22738c661dd
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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