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

HRID 1448524ノート

反応式

HRID 1448524 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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.

後処理

  1. customfreeze-dried

出典と根拠

ORDレコード
ord-93bd61f1dc72466f90d04284cee2883b
出典データセット
uspto-grants-1979_12
特許番号
US04180655

反応ノート

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