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

HRID 1448523ノート

反応式

HRID 1448523 の反応式
[C@@H:1]1([NH:12][C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[N:19]([O-])=[O:20].[Na+]>O.C(O)(=O)C>[C@@H:1]1([NH:12][C:13]([N:15]([N:19]=[O:20])[CH2:16][CH2:17][CH3:18])=[O:14])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

参加物

5

反応物 2

HCID 23668193Sodium NitriteHCID 536598611-(beta-D-glucopyranosyl)-3-n-propylurea

生成物 1

HCID 13345998N-propyl-N'(beta-D-glucosyl)-N-nitrosourea収率 81.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

1-(β-D-glucopyranosyl)-3-n-propylurea (1.50 g) was dissolved in a mixture of water (10 ml) and acetic acid (2 ml), and to the resulting solution was added 560 mg (1.5 mol. equivalents) of sodium nitrite at ambient temperature under stirring to effect the nitrosation. The reaction mixture was treated with Amberlite IR-120 (H+ form) for the removal of sodium ion and then concentrated to dryness below 35° C. and under a reduced pressure. Crystallisation of the residue from n-propanol gave 1.35 g of the titled compound. Yield 80%. mp. 112° C. (decomposition with foaming). [α]D21 -6° (c 1.0, H2O).

後処理

  1. concentrationconcentrated to dryness below 35° C. and under a reduced pressure
  2. customCrystallisation of the residue from n-propanol

出典と根拠

ORDレコード
ord-a4bdb17c62a3449d98cdd1eebaa0d127
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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