Sodium Nitrite → N-butyl-N'-(beta-D-glucosyl)-N-nitrosourea

HRID 1448524Notes

Reaction equation

HRID 1448524 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][C@@H:9]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]1[OH:11])=[O:7])[CH2:2][CH2:3][CH3:4].[N:20]([O-])=[O:21].[Na+]>O.C(O)(=O)C>[CH2:1]([N:5]([N:20]=[O:21])[C:6]([NH:8][C@@H:9]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]1[OH:11])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 539396901-n-butyl-3-(beta-D-glucopyranosyl)urea

Product 1

HCID 13346001N-butyl-N'-(beta-D-glucosyl)-N-nitrosoureaYield 90.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-n-butyl-3-(β-D-glucopyranosyl)urea (0.50 g) was dissolved in a mixture of water (2 ml) and acetic acid (2 ml), and to the resulting solution was added sodium nitrite (186 mg, 1.5 mol. equivalents). The nitrosation was conducted in the same manner as in Example 1(a). The reaction mixture was treated with Amberlite IR-120 (H+ form) for the removal of sodium cation and then freeze-dried, affording 0.5 g of the titled compound as a glassy substance of pale yellow color. [α]D26 -1.5° (c 1.0, H2O). This substance gave a single spot at Rf 0.51 in a thin layer chromatography on silica gel using chloroform-methanol (4:1 by volume) as eluent.

Workup

  1. customfreeze-dried

Sources & evidence

ORD record
ord-93bd61f1dc72466f90d04284cee2883b
Source dataset
uspto-grants-1979_12
Patent number
US04180655

Reaction notes

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