Sodium Sulfate → HCID 86616384, compound

HRID 505657Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][C:5]1[C:10]([CH2:11][CH3:12])=[C:9]([O:13][CH2:14][O:15][CH3:16])[CH:8]=[C:7]([O:17][CH2:18][O:19][CH3:20])[C:6]=1[C:21](=[O:30])[NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:23]([NH:22][C:21](=[O:30])[C:6]1[C:7]([O:17][CH2:18][O:19][CH3:20])=[CH:8][C:9]([O:13][CH2:14][O:15][CH3:16])=[C:10]([CH2:11][CH3:12])[C:5]=1[CH2:4][CH2:3][OH:2])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The above-obtained [2-(N-benzylcarbamoyl)-6-ethyl-3,5-bis(methoxymethoxy)phenyl]acetic acid methyl ester (46 mg, 0.11 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled to 0° C. The obtained solution was added with 1.0 mol/L lithium aluminum hydride-tetrahydrofuran solution (0.20 mL, 0.20 mmol) followed by stirring at 0° C. for 0.5 hour. The reaction mixture was added with saturated aqueous sodium sulfate solution, and was extracted with ethyl acetate 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to obtain N-benzyl-3-ethyl-2-(2-hydroxyethyl)-4,6-bis(methoxymethoxy)benzamide (30 mg, 74%).

Workup

extractionwas extracted with ethyl acetate 3 times
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-b4fa4359d2694b399e82322baf6bdb79
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781485B2

Reaction notes

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