Dimethylformamide diethylacetal → HCID 14372947, compound
Reaction equation
[C:1]([C:4]1[N:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]=1[CH2:17][O:18][CH3:19])=[CH:13][C:12]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:11][CH:10]=3)(=[O:3])[CH3:2].C(O[CH:31](OCC)[N:32](C)C)C>>[CH2:21]([O:20][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH:6]=[N:5][C:4]([C:1]3[O:3][N:32]=[CH:31][CH:2]=3)=[C:16]([CH2:17][O:18][CH3:19])[C:15]2=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1Participants
Procedure
At 100° C., 500 mg of 3-acetyl-6-benzyloxy-4-methoxymethyl-β-carboline is stirred overnight in 5 ml of N,N-dimethylformamide diethylacetal. After concentration by evaporation, the mixture, without further purification, is taken up in 20 ml of absolute ethanol, combined with 600 mg of hydroxylamine-O-sulfonic acid in 5 ml of methanol, and stirred for 5 hours at room temperature. After neutralization with triethylamine, the reaction mixture is stirred overnight, introduced into water, and extracted with ethyl acetate; the organic phase is dried over magnesium sulfate and concentrated under vacuum. After chromatography over silica gel with acetone:triethylamine in a ratio of 10:1 as the eluent, 130 mg of 6-benzyloxy-4-methoxymethyl-3-(5-isoxazolyl)-β-carboline is obtained, melting point 125°-126° C.
Workup
- concentrationAfter concentration
- customby evaporation
- customthe mixture, without further purification
- stirringAfter neutralization with triethylamine, the reaction mixture is stirred overnight
- additionintroduced into water
- extractionextracted with ethyl acetate
- dry with materialthe organic phase is dried over magnesium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-24a8bba81eea4b879fe7153557f44ff4
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04933345
Reaction notes
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