Diethyl Ether → N-{(S)-6-[(S)-1-((R)-2-Methylpropane-2-sulfinylamino)ethyl]-1,2,3,4-tetrahydro-naphthalen-2-yl}-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913820Notes

Reaction equation

HRID 1913820 reaction equation
[CH3:1][C:2]([S@:5](/[N:7]=[CH:8]/[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][C@@H:14]([NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@@H:29]3[CH2:33][CH2:32][CH2:31][O:30]3)=[CH:23][CH:22]=1)[CH2:13][CH2:12]2)=[O:6])([CH3:4])[CH3:3].[CH2:35](OCC)C.ClCCl.C[Mg]Br>O>[CH3:4][C:2]([S@:5]([NH:7][C@H:8]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][C@@H:14]([NH:19][C:20](=[O:34])[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C@@H:29]3[CH2:33][CH2:32][CH2:31][O:30]3)=[CH:25][CH:26]=1)[CH2:13][CH2:12]2)[CH3:35])=[O:6])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 87439525N-[(2S)-6-[(E)-[(R)-tert-butylsulfinyl]iminomethyl]-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[[(2S)-oxolan-2-yl]methoxy]benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 67545432N-{(S)-6-[(S)-1-((R)-2-Methylpropane-2-sulfinylamino)ethyl]-1,2,3,4-tetrahydro-naphthalen-2-yl}-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension, cooled to −45° C., of N-((S)-6-{[(E)-(R)-2-methylpropane-2-sulfinylimino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.34 g), diethyl ether (15 ml) and dichloromethane (15 ml) was admixed with methylmagnesium bromide (1.1 ml; 1.4 M in toluene). After warming to room temperature, the mixture was stirred for another 5 hours. The reaction mixture was hydrolyzed cautiously with water and extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate). The product was thus obtained with the molecular weight of 498.69 (C28H38N2O4S); MS (ESI): 499 (M+H+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate)
  6. customThe product was thus obtained with the molecular weight of 498.69 (C28H38N2O4S)

Sources & evidence

ORD record
ord-ecc952bd3a514fb39af2cea91675e194
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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