Tetrabutylammonium Fluoride → N-(2-Amino-2-oxoethyl)-2-(3-hydroxy-1-azetidinyl)-N-(1-methylethyl)-4-thiazolecarboxamide

HRID 891707Notes

Reaction equation

HRID 891707 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:37])[N:29]([CH2:33][C:34](=[O:36])[NH2:35])[CH:30]([CH3:32])[CH3:31])[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>[C:34]([CH2:33][N:29]([CH:30]([CH3:32])[CH3:31])[C:28]([C:26]1[N:27]=[C:23]([N:21]2[CH2:20][CH:19]([OH:18])[CH2:22]2)[S:24][CH:25]=1)=[O:37])(=[O:36])[NH2:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242735HCID 22242735, compound

Product 1

HCID 22242947N-(2-Amino-2-oxoethyl)-2-(3-hydroxy-1-azetidinyl)-N-(1-methylethyl)-4-thiazolecarboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(N-carbamoylmethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]azetidine (6.52 g, 11.8 mmol) (obtained as described in Reference Example 49(3)) in anhydrous tetrahydrofuran (326 ml) was added a 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (14.2 ml, 14.2 mmol) in an ice bath, and the mixture was stirred in the ice bath for 2 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:methanol (10:1) as the eluant to afford 1-[4-(N-carbamoylmethyl-N-isopropyl-carbamoyl)-1,3-thiazol-2-yl]-3-hydroxyazetidine (2.35 g, yield 67%) 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-a6b7f72ecccb4638b1697c0c651b5172
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…