2-Chloroethanol → HCID 118005630, compound

HRID 1488272Notes

Reaction equation

HRID 1488272 reaction equation
ClCCO.[Cl:5][C:6](Cl)(Cl)[C:7](=N)[O:8][CH:9]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]1[F:28].FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(Cl)Cl>[C:13]([O:12][C@H:11]1[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][CH:9]([O:8][CH2:7][CH2:6][Cl:5])[C@@H:10]1[F:28])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 65367Trimethylsilyl triflateHCID 118005600HCID 118005600, compound

Product 1

HCID 118005630HCID 118005630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloroethanol (1.0 mL, 14.92 mmol), 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-glucopyranosyl trichloroacetimidate (1.4 g, 3.09 mmol, Angew. Chem. Int. Ed. 2010, 49, 8724) and 4 Å molecular sieves in CH2Cl2 (50 mL) at −30° C. was added trimethylsilyl trifluoromethanesulfonate (0.25 mL, 1.384 mmol) dropwise. The mixture was allowed to gradually warm up to rt. After stirring for 2 hr, the reaction was quenched with TEA (0.13 mL, 0.933 mmol). The resulting mixture was filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (80 g), eluting with 0-60% EtOAc in hexanes to give the title compound. This anomeric mixture was used directly in the next step without further purification. TLC: silica gel, hexane/EtOAc: 3/1, Rf=0.35.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography on silica gel (80 g)
  4. washeluting with 0-60% EtOAc in hexanes

Sources & evidence

ORD record
ord-487d27367817478eb10403d15f57a76e
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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