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

HRID 1448524노트

반응식

HRID 1448524 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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.

후처리

  1. customfreeze-dried

출처 및 근거

ORD 기록
ord-93bd61f1dc72466f90d04284cee2883b
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04180655

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