Tetrabutylammonium Fluoride → HCID 69544027, compound

HRID 891627Notes

Reaction equation

HRID 891627 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:50])[NH:29][CH2:30][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:50])[NH:29][CH2:30][CH2:31][OH:32])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242991HCID 22242991, compound

Product 1

HCID 69544027HCID 69544027, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[2-(t-butyldiphenylsilyloxy)ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.68 g, 2.33 mmol) (obtained as described in Reference Example 33(2)) in anhydrous tetrahydrofuran (75 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (5.6 ml, 5.6 mmol) in an ice bath, and 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-hydroxyethylcarbamoyl-1,3-thiazol-2-yl)azetidine (481.2 mg, yield 85%) 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-82f5b276cf0d478b8758aad30df7c02a
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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