Nitrogen trioxide → HCID 131714705, compound

HRID 1981667Notes

Reaction equation

HRID 1981667 reaction equation
[N:1]([N+]([O-])=O)=[O:2].[CH:6]([N:9]([CH:16]([OH:31])[C@H:17]1[O:23][C@:21]([CH2:24][CH2:25][CH2:26][CH3:27])([OH:22])[C@H:20]([OH:28])[C@@H:19]([OH:29])[C@@H:18]1[OH:30])[C:10](=[O:15])[NH:11][CH2:12][CH2:13][Cl:14])([CH3:8])[CH3:7]>ClC(Cl)C>[CH:6]([N:9]([CH:16]([OH:31])[C@H:17]1[O:23][C@:21]([CH2:24][CH2:25][CH2:26][CH3:27])([OH:22])[C@H:20]([OH:28])[C@@H:19]([OH:29])[C@@H:18]1[OH:30])[C:10](=[O:15])[N:11]([CH2:12][CH2:13][Cl:14])[N:1]=[O:2])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 61526Nitrogen trioxideHCID 131714706HCID 131714706, compound

Product 1

HCID 131714705HCID 131714705, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dinitrogen trioxide gas (1.3 g) was introduced into a solution of the thus prepared 3-isopropyl-3-(n-butyl-α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (3.58 g, 9.35 mmol) in dichloroethane (50 ml) with thorough stirring at 15°-20° C., and stirring was continued for further two hours at the same temperature. The reaction mixture was vacuum-concentrated concentrated at 25° C., and purified by column chromatography (packing: silica gel; eluent: hexane/ethyl acetate 4:1) to obtain 3-isopropyl-3-(n-butyl-α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea (2.78 g, 6.75 mmol); yield 72.2%, m.p. 70°-72° C., [α]D20 +69.7° (C 1.0, methanol).

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture was vacuum-concentrated
  3. concentrationconcentrated at 25° C.
  4. custompurified by column chromatography (packing: silica gel; eluent: hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-72ea467539ea44df8d19858af2cedf6e
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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