Tetrabutylammonium Fluoride → HCID 69544233, compound

HRID 891642Notes

Reaction equation

HRID 891642 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:51])[NH:29][C@@H:30]([CH3:50])[CH2:31][O:32][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[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:51])[NH:29][C@@H:30]([CH3:50])[CH2:31][OH:32])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69543968HCID 69543968, compound

Product 1

HCID 69544233HCID 69544233, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S)-2-(t-butyldiphenylsilyloxy)-1-methylethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (2.77 g, 3.77 mmol) (obtained as described in Reference Example 35(2)) in anhydrous tetrahydrofuran (140 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (9.06 ml, 9.06 mmol) in an ice bath. The mixture was stirred in the ice bath for 3.5 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 using ethyl acetate→ethyl acetate:methanol (9:1) as the eluant to afford 3-hydroxy-1-[4-((1S)-2-hydroxy-1-methylethylcarbamoyl)-1,3-thiazol-2-yl]azetidine (911 mg, yield 94%) 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-c65b671199e84ebab15b151802530e58
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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