Nitrogen trioxide → HCID 131714707, compound

HRID 1981668Notes

Reaction equation

HRID 1981668 reaction equation
[N:1]([N+]([O-])=O)=[O:2].[CH2:6]([N:11]([CH:18]([OH:33])[C@H:19]1[O:25][C@:23]([CH2:26][CH2:27][CH2:28][CH3:29])([OH:24])[C@H:22]([OH:30])[C@@H:21]([OH:31])[C@@H:20]1[OH:32])[C:12](=[O:17])[NH:13][CH2:14][CH2:15][Cl:16])[CH2:7][CH:8]([CH3:10])[CH3:9]>O1CCCC1.C(O)(=O)C>[CH2:6]([N:11]([CH:18]([OH:33])[C@H:19]1[O:25][C@:23]([CH2:26][CH2:27][CH2:28][CH3:29])([OH:24])[C@H:22]([OH:30])[C@@H:21]([OH:31])[C@@H:20]1[OH:32])[C:12](=[O:17])[N:13]([CH2:14][CH2:15][Cl:16])[N:1]=[O:2])[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 61526Nitrogen trioxideHCID 131714708HCID 131714708, compound

Product 1

HCID 131714707HCID 131714707, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dinitrogen trioxide gas (0.6 g) was introduced into a solution of 3-isopentyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (2.15 g, 5.23 mmol), synthesized in the above-mentioned way, in a mixture of tetrahydrofuran (50 ml) and acetic acid (8 ml) with well stirring at 0° to 5° C. After continuation of stirring for 2 hours, the resulting solution was vacuum-concentrated at 25° C. and purified by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1), giving 1.44 g of 3-isopentyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea; yield 62.6%, m.p. 66°-68° C., [α]D20 +65.2° (C 1.0, methanol).

Workup

  1. stirringAfter continuation of stirring for 2 hours
  2. concentrationthe resulting solution was vacuum-concentrated at 25° C.
  3. custompurified by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1)

Sources & evidence

ORD record
ord-0486687136ff426481bdb2f6a0df7db6
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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