3-Nitrobenzoic acid → [(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-3-nitrobenzoate

HRID 1529526Notes

Reaction equation

HRID 1529526 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:22])[CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[OH:10].[N+:23]([C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](O)=[O:30])([O-:25])=[O:24].C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:21][C:6]1[CH:5]=[N+:4]([O-:22])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@H:9]([O:10][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=1)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1

Participants

6

Reactant 3

HCID 84973-Nitrobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86720690[(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]-3-nitrobenzoateYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (0.500 g, 1.45 mmol) and 3-nitrobenzoic acid (0.242 g, 1.45 mmol) in dichloromethane (15.0 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.560 g, 2.91 mmol) and N,N-dimethylpyridin-4-amine (0.089 g, 0.73 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (25.0 mL) and extracted with dichloromethane (×2). The combined organic extracts were dried on magnesium sulphate, filtered and the solvent removed in vacuo to afford a yellow oil. The crude material was purified by silica gel chromatography eluting sequentially with iso-hexane, ethyl acetate and 10% methanol in ethyl acetate to afford the title compound as a yellow solid (0.642 g, 90% yield).

Workup

  1. customThe reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (25.0 mL)
  2. extractionextracted with dichloromethane (×2)
  3. customThe combined organic extracts were dried on magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto afford a yellow oil
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting sequentially with iso-hexane, ethyl acetate and 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-72e89e8274404237a274b478f2fb78f2
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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