Tetrabutylammonium Fluoride → HCID 69543925, compound

HRID 891634Notes

Reaction equation

HRID 891634 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:52])[NH:29][C@H:30]([CH2:33][O:34][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:31][CH3:32])[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:52])[NH:29][C@H:30]([CH2:33][OH:34])[CH2:31][CH3:32])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69543899HCID 69543899, compound

Product 1

HCID 69543925HCID 69543925, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S)-1-(t-butyldiphenylsilyloxymethyl)-propylcarbamoyl]-1,3-thiazol-2-yl}azetidine (2.52 g, 3.50 mmol) (obtained as described in Reference Example 34(2)) in anhydrous tetrahydrofuran (126 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (8.40 ml, 8.40 mmol) in an ice bath. The mixture was stirred overnight. 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→ethyl acetate:methanol (9:1) as the eluant to afford 3-hydroxy-1-{4-[(1S)-1-(hydroxymethyl)-propylcarbamoyl]-1,3-thiazol-2-yl}azetidine (947 mg, yield 100%) as a pale yellow oil.

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-d0c166a158da47d3826c2390d1481d45
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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