Triacetoxyperiodinane → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-(5-formyl-2-thienyl)acetate

HRID 2279950Notes

Reaction equation

HRID 2279950 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:32])[CH:5]=[C:6]([Cl:31])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:30])[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]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:31][C:6]1[CH:5]=[N+:4]([O-:32])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:30])[CH2:22][C:23]1[S:24][C:25]([CH:28]=[O: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]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 130473176[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-(hydroxymethyl)-2-thienyl]acetate

Product 1

HCID 130473073[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-(5-formyl-2-thienyl)acetateYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]2-[5-(hydroxymethyl)-2-thienyl]acetate (100 mg, 0.20 mmol) in dichloromethane (2 mL) was added Dess-Martin periodinane (102 mg, 0.24 mmol) at −78° C. The reaction was stirred at room temperature for 30 min. The reaction solution was washed with saturated aqueous Na2S2O3 (5 mL) and saturated aqueous sodium bicarbonate (5 mL). The organic phase was passed through a hydrophobic fit and concentrated in vacuo to give the title compound as a pale yellow oil (100 mg, quantitative yield) which was used in the next step without further purification.

Workup

  1. washThe reaction solution was washed with saturated aqueous Na2S2O3 (5 mL) and saturated aqueous sodium bicarbonate (5 mL)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ddd31de75b147ba9f20bff73e0e66f9
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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