Tetrabutylammonium Fluoride → HCID 56627540, compound

HRID 1196217Notes

Reaction equation

HRID 1196217 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([C@H:8]1[N:11]([Si](C(C)(C)C)(C)C)[C:10](=[O:19])[C@@H:9]1[C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH3:21])[CH3:7])=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]([C@H:8]1[NH:11][C:10](=[O:19])[C@@H:9]1[C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[CH3:21])[CH3:7])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 56605782HCID 56605782, compound

Product 1

HCID 56627540HCID 56627540, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S,4S)-4-(1-ethoxycarbonylethyl)-3-(1-(R)-t-butyldimethylsilyloxyethyl)-1-t-butyldimethylsilyl-2-azetidinone (46.3 g) in dry tetrahydrofuran (60 ml) was treated with a 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride (96 ml) at room temperature for 45 minutes. The reaction mixture was diluted with ethyl acetate (250 ml) and washed with brine (60 ml). The washing was extracted with ethyl acetate (50 ml). The extract and the ethyl acetate layer were combined together, washed with brine and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave an oily residue, which was purified by silica gel chromatography to yield (3S,4S)-4-(1-ethoxycarbonylethyl)-3-(1-(R)-t-butyldimethylsilyloxyethyl)-2-azetidinone.

Workup

  1. washwashed with brine (60 ml)
  2. extractionThe washing was extracted with ethyl acetate (50 ml)
  3. extractionThe extract
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationFiltration and concentration of the filtrate in vacuo
  7. customgave an oily residue, which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-32c8f7a7b3d94a03baaaef3984ae275d
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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