Tetrabutylammonium Fluoride → HCID 69544218, compound

HRID 891663Notes

Reaction equation

HRID 891663 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:54])[NH:29][C@H:30]([CH2:35][O:36][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[C@@H:31]([CH3:34])[CH2:32][CH3:33])[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:54])[NH:29][C@H:30]([CH2:35][OH:36])[C@@H:31]([CH3:34])[CH2:32][CH3:33])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69583523HCID 69583523, compound

Product 1

HCID 69544218HCID 69544218, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S,2S)-1-(t-butyldiphenylsilyloxymethyl)-2-methylbutylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.89 g, 2.45 mmol) (obtained as described in Reference Example 38(2)) in anhydrous tetrahydrofuran (95 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (5.87 ml, 5.87 mmol) in an ice bath. The mixture was stirred in the ice bath 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,2S)-1-(hydroxymethyl)-2-methylbutylcarbamoyl]-1,3-thiazol-2-yl}azetidine (811 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-fa60e6449d97474c8f01a43a9dc50e18
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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