HCID 131733498, compound → HCID 130473053, compound

HRID 2279962Notes

Reaction equation

HRID 2279962 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:39])[CH:5]=[C:6]([Cl:38])[C:7]=1[CH2:8][C@H:9]([O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][CH2:29][O:30][Si](C(C)(C)C)(C)C)=[CH:26][CH:27]=1)=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1>N1C=CC=CC=1>[Cl:38][C:6]1[CH:5]=[N+:4]([O-:39])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@H:9]([O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][CH2:29][OH:30])=[CH:26][CH:27]=1)=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

3

Reactant 1

HCID 131733498HCID 131733498, compound

Product 1

HCID 130473053HCID 130473053, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]thiophene-2-carboxylate (400 mg, 0.65 mmol) in pyridine (6 mL) was added HF.pyridine (0.88 ml) dropwise and the mixture was allowed to stir at room temperature for 3 h. The mixture was cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate solution (10 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic fractions were passed through a hydrophobic fit and the solvent was removed by evaporation under reduced pressure. The crude material was purified by silica gel column chromatography, eluting with 0-100% ethyl acetate/10% methanol in ethyl acetate, to afford the title compound (323 mg, quantitative yield) as a white solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with saturated aqueous sodium bicarbonate solution (10 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 0-100% ethyl acetate/10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-820329b44fda4e5099719a7aa0a1ae88
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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