Selectfluor → HCID 44571539, compound

HRID 640055Notes

Reaction equation

HRID 640055 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:8][S:9]([C:12]1[S:13][C:14]([Sn](C)(C)C)=[CH:15][CH:16]=1)(=[O:11])=[O:10])[C@@H:4]([CH3:7])[CH2:5][CH3:6].[B-](F)(F)(F)[F:22].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.CCOC(C)=O.CCCCCC>C(#N)C>[F:22][C:14]1[S:13][C:12]([S:9]([NH:8][C@H:3]([CH2:2][OH:1])[C@@H:4]([CH3:7])[CH2:5][CH3:6])(=[O:11])=[O:10])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 2724933SelectfluorHCID 21226206Ethyl acetate hexane2×HCID 66929701HCID 66929701, compound

Product 1

HCID 44571539HCID 44571539, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-[(1S,2S)-1-(hydroxymethyl)-2-methylbutyl]-5-(trimethylstannyl)-2-thiophene sulfonamide (1.0 g, 2.34 mmol) in dry acetonitrile (20 mL) was stirred under nitrogen at 25° C. Selectfluor (0.850 g, 2.40 mL) was added in one portion and the solution stirred for 19 h at 25° C. After 3 h a white precipitate began to appear. An aliquot was taken and TLC (1:1 EtOAc-hexane) indicated that reaction was not complete. Mainly, starting material was present. The reaction was heated to 80° C. for 6 h. An aliquot was taken and TLC (1:1 EtOAc-hexane) indicated that reaction was complete. The slurry was then filtered and the solvent removed in vacuo to obtain a crude yellow oil (0.6 g). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluent: 1:2 EtOAc-hexane to obtain 5-fluoro-N-[(1S,2S)-1-(hydroxymethyl)-2-methyl-butyl]-2-thiophenesulfonamide as an amorphous white solid (0.102 g, 15.49%). Mass Spectrum (−ESI): 280 (M−H)−. Anal. Calc'd for C10H16NFO4S2: C, 42.69; H, 5.73; N, 4.98. Found: C, 42.47; H, 5.74; N, 4.87.

Workup

  1. waitAfter 3 h a white precipitate began
  2. temperatureThe reaction was heated to 80° C. for 6 h
  3. filtrationThe slurry was then filtered
  4. customthe solvent removed in vacuo
  5. customto obtain a crude yellow oil (0.6 g)
  6. customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluent

Sources & evidence

ORD record
ord-fcabfd20f0a344c4a70ba41404d93530
Source dataset
uspto-grants-2010_04
Patent number
US07691884B2

Reaction notes

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