Sodium hydride → HCID 19596599, compound

HRID 612934Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][SH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][N:16]=1>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][S:11][C:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 5 °C

Procedure

2-(N-tert-Butoxycarbonylamino)ethanethiol (300 mg) was dissolved in dimethylformamide (3.0 ml), and the mixture was cooled to 5° C., followed by addition of sodium hydride [>55% (oil), 73 mg]. The resulting mixture was stirred at the same temperature for 30 minutes. Then, 3-chloro-5-phenylisoxazole (300 mg) was added to the reaction mixture, followed by stirring of the mixture at the same temperature for 30 minutes and further at room temperature for 3 days. At the end of this time, the reaction mixture was added to ice-cold water (40 ml) and extracted with ethyl acetate (40 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain the title compound (130 mg, 24%) as colorless crystals.

Workup

stirringby stirring of the mixture at the same temperature for 30 minutes and further at room temperature for 3 days
extractionextracted with ethyl acetate (40 ml×2)
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-bc80da1c73274255897be83fb21399f3
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06005116

Reaction notes

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