Tetrabutylammonium Fluoride → 3-Hydroxy-azetidine-1-carboxylic acid [5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

HRID 2247378Notes

Reaction equation

HRID 2247378 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13][C:14]([N:16]3[CH2:19][CH:18]([O:20][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:17]3)=[O:15])=[N:10][C:9]=2[CH3:38])=[CH:4][C:3]=1[S:39]([CH3:42])(=[O:41])=[O:40].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13][C:14]([N:16]3[CH2:17][CH:18]([OH:20])[CH2:19]3)=[O:15])=[N:10][C:9]=2[CH3:38])=[CH:4][C:3]=1[S:39]([CH3:42])(=[O:41])=[O:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 865984283-(tert-Butyl-diphenyl-silanyloxy)-azetidine-1-carboxylic acid [5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazole-2-yl]amide

Product 1

HCID 865984293-Hydroxy-azetidine-1-carboxylic acid [5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3-(tert-butyl-diphenyl-silanyloxy)-azetidine-1-carboxylic acid [5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazole-2-yl]amide (162c) (0.15 g, 0.23 mmol) in THF (2 ml) at room temperature is treated with tetrabutylammonium fluoride (1.0 M in THF, 0.23 ml, 0.23 mmol). After 30 minutes, the reaction was complete. Purification by preparative LC-MS affords the titled compound.

Workup

  1. customPurification by preparative LC-MS

Sources & evidence

ORD record
ord-18aa53a4984a4507bbc0cfb3b23ccf56
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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