Hydrochloric Acid → (3RS)-1-(2-acetylthiophen-3-yl)methyl-3-amino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one
Reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14]([CH:21]([CH3:23])[CH3:22])=[N:13][CH:12]([NH:24]C(OC(C)(C)C)=O)[C:11]1=[O:32])(=[O:3])[CH3:2].Cl>C(OCC)(=O)C>[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14]([CH:21]([CH3:22])[CH3:23])=[N:13][CH:12]([NH2:24])[C:11]1=[O:32])(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3RS)-1-(2-acetylthiophen-3-yl)methyl-3-tert-butoxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (0.370 g) in ethyl acetate (50 ml) was treated with gaseous hydrogen chloride at 5˜10° C. in an ice-bath for 30 minutes. The resultant mixture was extracted with 3N aqueous hydrochloric acid (2×10 ml). The aqueous layer was basified with sodium hydrogen carbonate and extracted with ethyl acetate (2×50 ml). The extracts were combined, over sodium sulfate, filtered and concentrated in vacuo to afford (3RS)-1-(2-acetylthiophen-3-yl)methyl-3-amino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (0.230 g), which was used in a following reaction step without further purification.
Workup
- extractionThe resultant mixture was extracted with 3N aqueous hydrochloric acid (2×10 ml)
- extractionextracted with ethyl acetate (2×50 ml)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cd1a7c0e24c94279b8dc9b0a3a865d6d
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291452B1
Reaction notes
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