Methanol → 2-[3-(2-Chloroethyl)-3-nitrosoureido]-D-glucopyranose
Reaction equation
[NH2:1][C@@H:2]1[C@@H:8]([OH:9])[C@H:7]([OH:10])[C@@H:6]([CH2:11][OH:12])[O:5][CH:3]1[OH:4].[Cl:13][CH2:14][CH2:15][N:16]([N:29]=[O:30])[C:17](=O)[O:18]C1C=CC=CC=1[N+]([O-])=O.C[OH:32]>CS(C)=O.C(Cl)Cl.O1CCCC1>[OH:4][CH:3]1[O:5][C@H:6]([CH2:11][OH:12])[C@@H:7]([OH:10])[C@H:8]([OH:9])[C@@:2]1([NH:1][C:17](=[O:18])[N:16]([CH2:15][CH2:14][Cl:13])[N:29]=[O:30])[OH:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
1.79 g (10 mmol) of 2-amino-2-deoxy-D-glucopyranose is dissolved in a mixture of 10 ml methanol and 5 ml dimethyl sulfoxide, and this solution is added dropwise to a solution prepared by dissolving 3.28 g (12 mmol) of o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate in a mixture of 10 ml methylene chloride and 10 ml tetrahydrofuran, while stirring, at 20°-25° C. over 10 minutes. The resultant mixture is stirred at the same temperature for a further 1.5 hours. The thus reacted solution is concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with petroleum ether, dried under reduced pressure, and recrystallized from ethanol to give 2.56 g of 3-(D-glucopyranos-2-yl)-1-(2-chloroethyl)-1-nitrosourea. Yield 81.6%. mp 147°-148° C. (decomp.). Analysis for C9H16N3O7Cl (MW 313.69):
Workup
- additionthis solution is added dropwise to a solution
- customprepared
- concentrationThe thus reacted solution is concentrated at 40° C.
- customThe crystalline residue obtained
- washis washed with petroleum ether
- customdried under reduced pressure
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-41a0dc85a9f2440496bc8d44df4663a2
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04156777
Reaction notes
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