HCID 21201810, compound → 1-(2-thenoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979349Notes

Reaction equation

[C:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=3[N:13]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:12][CH:11]([NH:27]C(OC(C)(C)C)=O)[C:10]2=[O:35])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1>Cl.O1CCOCC1>[C:1]1([C:6]([CH2:8][N:9]2[C:15]3[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=3[N:13]([C:21](=[O:26])[C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:12][CH:11]([NH2:27])[C:10]2=[O:35])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 55 °C

Procedure

1-(2-Thenoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.00 g) was dissolved in 4N HCl-dioxane (10 ml), the solution was stirred for one hour at 55° C. The reaction mixture was concentrated under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate, extracted with methylene chloride. The organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, to thereby obtain 0.74 g of the titled compound as brown crystals (Yield: 92%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with methylene chloride
washThe organic layer was successively 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-d71b192048f34f749e24c31e924bd0da
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239131B1

Reaction notes

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