(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 53888673, compound
Reaction equation
[OH:1][CH2:2][C@H:3]([NH:8][C:9]([C:11]1[N:12]=[CH:13][N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18](=[O:25])[N:17]([CH3:26])[CH2:16][C:15]=12)=O)[C:4]([O:6][CH3:7])=[O:5].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1.ClCCl>[CH3:26][N:17]1[C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:14]2[CH:13]=[N:12][C:11]([C:9]3[O:1][CH2:2][C@@H:3]([C:4]([O:6][CH3:7])=[O:5])[N:8]=3)=[C:15]2[CH2:16]1Participants
Procedure
A solution of 10.0 g (0.0279 mol) of methyl (S)-3-hydroxy-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-ylcarbonylamino)-propionate in 500 ml of tetrahydrofuran was treated while gassing with argon with 7.25 g (0.0304 mol) of methoxycarbonylsulphamoyl-triethylammonium hydroxide internal salt (Burgess reagent) according to the method described in Tetr. Letters 1992, 33, 907. The mixture was boiled at reflux for 1 hr. and completely freed from the solvents. The residue was dissolved in dichloromethane and chromatographed over silica gel with ethyl acetate/ethanol 9:1 as the eluent. There were obtained 4.4 g (46%) of methyl (S)-2-(5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-4,5-dihydro-oxazole-4-carboxylate as a white solid. An analytical sample was recrystallized from ethanol/diethyl ether and gave white crystals; m.p. 190-192°. [α]D20 =+45.4° (CHCl3, c=1%).
Workup
- temperatureat reflux for 1 hr
- customchromatographed over silica gel with ethyl acetate/ethanol 9:1 as the eluent
Sources & evidence
- ORD record
- ord-b0ab65b132774ff8a99ae2351264a6f6
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962450
Reaction notes
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