Tetrabutylammonium Fluoride → HCID 69544180, compound

HRID 891656Notes

Reaction equation

HRID 891656 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)[CH2:31][CH:32]([CH3:34])[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])[CH2:31][CH:32]([CH3:34])[CH3:33])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69543912HCID 69543912, compound

Product 1

HCID 69544180HCID 69544180, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S)-1-(t-butyldiphenylsilyloxymethyl)-3-methylbutylcarbamoyl]-1,3-thiazol-2-yl}azetidine (2.14 g, 3.72 mmol) (obtained as described in Reference Example 37(2)) in anhydrous tetrahydrofuran (107 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (8.94 ml, 8.94 mmol) in an ice bath. The mixture was stirred in the ice bath for 4 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)-1-(hydroxymethyl)-3-methyl-butylcarbamoyl]-1,3-thiazol-2-yl}azetidine (825 mg, yield 74%) 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-ca33a4bb339d440891cc7e2b20a9acdb
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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