1,2-Dichloroethane → HCID 86720280, compound

HRID 1754320Notes

Reaction equation

HRID 1754320 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[C:17]([OH:19])=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].[Cl:20][C:21]1[CH:22]=[N+:23]([O-:41])[CH:24]=[C:25]([Cl:40])[C:26]=1[CH2:27][C@@H:28]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=1)O.C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:40][C:25]1[CH:24]=[N+:23]([O-:41])[CH:22]=[C:21]([Cl:20])[C:26]=1[CH2:27][C@H:28]([O:18][C:17]([C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[S:9]([C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][CH:7]=1)(=[O:10])=[O:11])=[O:19])[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 86720279HCID 86720279, compound

Product 1

HCID 86720280HCID 86720280, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2S)-1-(4-formylphenyl)sulfonylpyrrolidine-2-carboxylic acid (283 mg, 1 mmol) in DMF (15 mL) was added (1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (344 mg, 1 mmol), followed by DMAP (60 mg, 0.5 mmol) and EDC (385 mg, 2 mmol). The mixture was allowed to stir at room temperature for 18 hours and then the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (15 mL) and saturated sodium bicarbonate solution (15 mL). The organic phase was passed through a hydrophobic fit and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography, eluting with 0-100% EtOAc in isohexane followed by 10% methanol in DCM, to afford the title compound as an off-white solid (333 mg, 55%).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (15 mL) and saturated sodium bicarbonate solution (15 mL)
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with 0-100% EtOAc in isohexane

Sources & evidence

ORD record
ord-cb5dedaa3e454eebb7098aec90499a8b
Source dataset
uspto-grants-2015_10
Patent number
US09169245B2

Reaction notes

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