Tetrahydrofuran → HCID 69544119, compound

HRID 891648Notes

Reaction equation

HRID 891648 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:52])[NH:29][C@@H:30](O[Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:31]([CH3:33])[CH3:32])[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.[O:71]1CCC[CH2:72]1>>[OH:18][CH:19]1[CH2:20][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:52])[NH:29][C@H:30]([CH2:72][OH:71])[CH:31]([CH3:32])[CH3:33])[N:27]=2)[CH2:22]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 69544058HCID 69544058, compound

Product 1

HCID 69544119HCID 69544119, compoundYield 100%

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[(1S)-1-(t-butyldiphenylsilyloxy)-2-methylpropylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.98 g, 2.60 mmol) (obtained as described in Reference Example 36(2)) in anhydrous tetrahydrofuran (100 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (6.23 ml, 6.23 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 (95:5) as the eluant to afford 3-hydroxy-1-{4-[(1S)-1-(hydroxymethyl)-2-methylpropylcarbamoyl]-1,3-thiazol-2-yl}azetidine (755 mg, yield 100%) as a colorless 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-1dbd0f103de94f95afcb43c0d9c43c33
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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