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

HRID 2083776노트

반응식

HRID 2083776 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c1a31d2d350a4b5399a3c30c109ae670
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04086415

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