Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-[(2S)-6-[(E)-[(R)-tert-butylsulfinyl]iminomethyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[[(2S)-oxolan-2-yl]methoxy]benzamide

HRID 1913821Notes

Reaction equation

HRID 1913821 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@@H:8]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][CH:16]=1)[CH2:7][CH2:6]2)=O.[CH3:29][C:30]([S@:33]([NH2:35])=[O:34])([CH3:32])[CH3:31].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>S([O-])([O-])(=O)=O.[Cu+2].ClCCl>[CH3:29][C:30]([S@:33](/[N:35]=[CH:1]/[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@@H:8]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][CH:16]=1)[CH2:7][CH2:6]2)=[O:34])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 86762190N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Product 1

HCID 87439525N-[(2S)-6-[(E)-[(R)-tert-butylsulfinyl]iminomethyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[[(2S)-oxolan-2-yl]methoxy]benzamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (1.0 g), (R)-2-methylpropane-2-sulfinic acid amide (0.32 g), pyridinium para-toluenesulfonate (165 mg), copper(II) sulfate (1.0 g; anhydrous) and dichloromethane (10 ml) was stirred for 24 hours. Solid fractions were filtered off and the filtrate was concentrated. The residue was purified by chromatography on silica gel. The product was thus obtained with the molecular weight of 482.65 (C27H34N2O4S); MS (ESI): 483 (M+H+).

Workup

  1. filtrationSolid fractions were filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel
  4. customThe product was thus obtained with the molecular weight of 482.65 (C27H34N2O4S)

Sources & evidence

ORD record
ord-2c342dcd6c9c4532b6dbd9067ebf06ea
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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