Methanol → 5-Acetoxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester
Reaction equation
C(OC(N=NC(OCC)=O)=O)C.[CH2:13]([O:15][C:16]([CH:18]1[CH:30]([CH2:31][O:32][CH3:33])[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][C:27]=3[CH2:34][O:35][C:36](=[O:38])[CH3:37])[NH:22][C:21]=2[CH:20](C(O)=O)[NH:19]1)=[O:17])[CH3:14].ClCCl.CO>O=O>[CH2:13]([O:15][C:16]([C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:23]3[C:28]([C:29]=2[C:30]=1[CH2:31][O:32][CH3:33])=[C:27]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH:26]=[CH:25][CH:24]=3)=[O:17])[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
90% Azodicarboxylic acid diethyl ester (76 ml) without addition of heat with stirring is added drop by drop to a solution of 5-acetoxymethyl-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid-3-ethyl ester (75 g) in oxygen-free dichloromethane (0.6 l) under argon protection. The temperature rises about 10° C. Reflux is performed for about 9 hours, then the mixture is left at room temperature for 60 hours. The precipitate is suctioned off, further end product can be obtained from the evaporated mother liquor after chromatography on silica gel with a mixture of dichloromethane (95%) with methanol (5%). Altogether 65 g of the title compound in the form of colorless crystals with a melting point of 129°-133° C. is obtained.
Workup
- temperatureof heat
- customrises about 10° C
- temperatureReflux
- waitthe mixture is left at room temperature for 60 hours
- customfurther end product can be obtained from the evaporated mother liquor after chromatography on silica gel
Sources & evidence
- ORD record
- ord-c9c8f4abbac041a0bf1cdb8b0633c1d3
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731365
Reaction notes
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