Tetrabutylammonium Fluoride → HCID 90295621, compound

HRID 1050221Notes

Reaction equation

HRID 1050221 reaction equation
[O:1]([C@@H:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:26]=[CH:27][C:28]3[N:33]4[C:34](=[O:47])[O:35][C@@H:36]([CH2:37][NH:38][C:39]([C:41]5[S:42][C:43]([Cl:46])=[CH:44][CH:45]=5)=[O:40])[C@@H:32]4[CH2:31][O:30][C:29]=3[CH:48]=2)[C:21](=[O:49])[CH2:20]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:46][C:43]1[S:42][C:41]([C:39]([NH:38][CH2:37][C@H:36]2[C@H:32]3[N:33]([C:28]4[CH:27]=[CH:26][C:25]([N:22]5[CH2:23][CH2:24][C@@H:19]([OH:1])[CH2:20][C:21]5=[O:49])=[CH:48][C:29]=4[O:30][CH2:31]3)[C:34](=[O:47])[O:35]2)=[O:40])=[CH:45][CH:44]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90295759HCID 90295759, compound

Product 1

HCID 90295621HCID 90295621, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound N-(((3S,3aS)-7-((R)-4-(t-butyldiphenylsiloxy)-2-oxopiperidin-1-yl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)-5-chlorothiophene-2-carboxamide (0.36 g, 0.502 mmol) was dissolved in THF. TBAF (1M/L, 0.50 ml) was added and stirred at room temperature for 2 h. After the reaction completed, the resulting mixture was washed with water, extracted with EA (20 ml×4), dried over anhydrous sodium sulfate, and dried by spinning. Column chromatography afforded white solid 0.13 g, yield 56.2%.

Workup

  1. washthe resulting mixture was washed with water
  2. extractionextracted with EA (20 ml×4)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customdried

Sources & evidence

ORD record
ord-0d290335cf7f44a38191a8e750858d88
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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