HCID 21201907, compound → 1-(5-methylfuran-2-yl)carbonylmethyl-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979444Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][CH:12]([NH:28]C(OC(C)(C)C)=O)[C:11]2=[O:36])=[O:8])=[CH:4][CH:3]=1>Cl.O1CCOCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[N:14]([C:22](=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:13][CH:12]([NH2:28])[C:11]2=[O:36])=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

1-(5-Methylfuran-2-yl)carbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.89 g) was dissolved in 4N HCl-dioxane (10 ml), the mixture was stirred at 40-50° C. for 20 minutes. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with saturated aqueous sodium bicarbonate, extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, to thereby obtain 0.71 g of title compound (Yield: 100%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-80f6bc041a4845f89905b14109de98bd
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Reaction notes

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