Water → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl] 4-(1,3-dioxolan-2-ylmethyl)benzoate

HRID 1529537Notes

Reaction equation

HRID 1529537 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[Cl:16][C:17]1[CH:18]=[N+:19]([O-:37])[CH:20]=[C:21]([Cl:36])[C:22]=1[CH2:23][C@@H:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1)O.CCN=C=NCCCN(C)C.Cl.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][C@H:24]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[CH2:23][C:22]2[C:21]([Cl:36])=[CH:20][N+:19]([O-:37])=[CH:18][C:17]=2[Cl:16])=[O:12])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 247269914-(1,3-Dioxolan-2-ylmethyl)benzoic acidHCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86720696[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl] 4-(1,3-dioxolan-2-ylmethyl)benzoateYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-((1,3-dioxolan-2-yl)methyl)benzoic acid (362 mg, 1.05 mmol) in DCM (9 mL) was added (1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (200 mg, 0.96 mmol) followed by DMAP (58 mg, 0.48 mmol) and EDC.HCl (396 mg, 1.9 mmol). The mixture was allowed to stir a room temperature for 18 hours and then water (20 mL) and DCM (20 mL) were added and the organic phase was passed through a hydrophobic frit. The solvent was removed in vacuo and the crude material was purified by silica gel column chromatography, eluting with 30-100% EtOAc in DCM, to afford the title compound as an off-white solid (497 mg, 97%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material was purified by silica gel column chromatography
  3. washeluting with 30-100% EtOAc in DCM

Sources & evidence

ORD record
ord-27f85e65983d4f3fb14a301f613016ca
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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