[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-thienyl]acetate → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-(hydroxymethyl)-2-thienyl]acetate
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](=[O:37])[CH2:22][C:23]1[S:24][C:25]([CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:26][CH:27]=1)[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](=[O:37])[CH2:22][C:23]1[S:24][C:25]([CH2:28][OH:29])=[CH:26][CH:27]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-thienyl]acetate (400 mg, 0.65 mmol) in pyridine (5 mL) was added HF.pyridine (0.88 mL) drop wise. The resultant solution was stirred at room temperature for 3 h. The reaction solution was cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate (5 mL). The aqueous phase was extracted with ethyl acetate (3×10 mL) and the organic phases combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a pale yellow solid (270 mg, 84%) which was used in the next step without further purification.
Workup
- customquenched with saturated aqueous sodium bicarbonate (5 mL)
- extractionThe aqueous phase was extracted with ethyl acetate (3×10 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-482c9c3aa49645a3bda0fcbacfe2c6d9
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133185B2
Reaction notes
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