Tetrabutylammonium Fluoride → HCID 22242958, compound

HRID 891616Notes

Reaction equation

HRID 891616 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:33][CH:32]([O:34][CH3:35])[CH2:31]3)=[O:29])[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]([N:30]3[CH2:33][CH:32]([O:34][CH3:35])[CH2:31]3)=[O:29])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242760HCID 22242760, compound

Product 1

HCID 22242958HCID 22242958, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-thiazol-2-yl]azetidine (870 mg, 1.71 mmol) (obtained as described in Reference Example 31(2)) in anhydrous tetrahydrofuran (45 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (2.06 ml, 2.06 mmol) in an ice bath, and then the mixture was stirred for 30 minutes. 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 (9:1) as the eluant to afford 3-hydroxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-thiazol-2-yl]azetidine (481 mg, 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-bb58c0046e57487ab62e9571e813b49e
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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