Tetrabutylammonium Fluoride → HCID 86587203, compound

HRID 478912Notes

Reaction equation

HRID 478912 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH:33]([O:48][Si](C(C)(C)C)(C)C)[CH2:34][NH:35][C:36]([C:38]2[CH:47]=[CH:46][C:41]3[NH:42][C:43](=[O:45])[O:44][C:40]=3[CH:39]=2)=[S:37])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.CCOC(C)=O>[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH:33]([OH:48])[CH2:34][NH:35][C:36]([C:38]2[CH:47]=[CH:46][C:41]3[NH:42][C:43](=[O:45])[O:44][C:40]=3[CH:39]=2)=[S:37])[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86587201HCID 86587201, compound

Product 1

HCID 86587203HCID 86587203, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (TBAF) (1.24 μmol, 1.24 mL, 1 M in THF) was added to a mixture of 2-oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide (336 mg, 623 μmol) and 4 Å molecular sieves (1 g) in THF (2 mL). After stirring at room temperature for 1.5 hours, the mixture was diluted with EtOAc, washed with saturated NaHCO3, brine and dried (MgSO4) to yield 2-oxo-2,3-dihydrobenzoxazole-6-carbothioic acid [3-(4-benzylpiperidin-1-yl)-2-hydroxypropyl]amide (280 mg, quantitative) as a solid yellow foam:

Workup

  1. washwashed with saturated NaHCO3, brine
  2. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-4517d3db6c5e45a9aec546314736c4fc
Source dataset
uspto-grants-2003_11
Patent number
US06642256B2

Reaction notes

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