Tetrabutylammonium Fluoride → HCID 86695419, compound

HRID 525529Notes

Reaction equation

HRID 525529 reaction equation
[F:1][CH:2]([F:37])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:22][C:21]([CH2:23][O:24][Si](C(C)C)(C(C)C)C(C)C)=[N:20][CH:19]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:36])[CH3:35])=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OC(=O)C)C>[F:37][CH:2]([F:1])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:22][C:21]([CH2:23][OH:24])=[N:20][CH:19]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:35])[CH3:36])=[O:4]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695420HCID 86695420, compound

Product 1

HCID 86695419HCID 86695419, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,2-difluoro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(2-((triisopropylsilyloxy)methyl)thiazol-5-yl)phenyl)oxazolidin-3-yl)ethanone (2.6 g, 4.8 mmol) in tetrahydrofuran (50 mL) is added tetrabutylammonium fluoride (5.2 mL of a 1M solution). The reaction is stirred at room temperature for 1 hour. The reaction is diluted with ethylacetate (100 mL) and washed with water and brine. The organic phase is dried (Na2SO4) and concentrated under vacuum. The crude material is chromatographed eluting from 100% hexanes to 75:25 ethylacetate:hexanes to afford the title compound (1.8 g): m/z (Cl) M+H 401.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. concentrationconcentrated under vacuum
  4. customThe crude material is chromatographed
  5. washeluting from 100% hexanes to 75:25 ethylacetate

Sources & evidence

ORD record
ord-386775b6aa2c4bfa9b0482fde1019699
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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