1,2-Dichloroethane → Tert-butyl (R)-(1-(3-methyl-1,2,4-oxadiazol-5-YL)ethyl)carbamate

HRID 1909104Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14](=[N:17]O)([NH2:16])[CH3:15].C(Cl)CCl.C(OCC)(=O)C>O1CCOCC1.CN(C)C=O>[CH3:15][C:14]1[N:17]=[C:11]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:10])[O:13][N:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(tert-butoxycarbonyl)-D-alanine (20 g, 106 mmol), acetamide oxime (17.3 g, 234 mmol) in 120 mL of 1,4-dioxane and 30 mL of N,N-dimethylformamide were added EDC (44.8 g, 234 mmol). The mixture was heated at 60° C. for 4 h then at 100° C. for 16 h. After cooling to ambient temperature, 300 mL of ethyl acetate was added. The mixture was washed with aqueous saturated sodium bicarbonate (2×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) to give pure tert-butyl [(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]carbamate (6.0 g). MS 172.1 ((M-t-butyl+H)+1).

Workup

temperatureAfter cooling to ambient temperature
washThe mixture was washed with aqueous saturated sodium bicarbonate (2×)
dry with materialThe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

Sources & evidence

ORD record: ord-a182c4c5c09443dd85e7e23f2a174208
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598209B2

Reaction notes

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