Sodium Nitrite → HCID 131714705, compound

HRID 1981666Notes

Reaction equation

HRID 1981666 reaction equation
[N:1]([O-:3])=O.[Na+].[CH:5]([N:8]([CH:15]([OH:30])[C@H:16]1[O:22][C@:20]([CH2:23][CH2:24][CH2:25][CH3:26])([OH:21])[C@H:19]([OH:27])[C@@H:18]([OH:28])[C@@H:17]1[OH:29])[C:9](=[O:14])[NH:10][CH2:11][CH2:12][Cl:13])([CH3:7])[CH3:6]>C(O)(=O)C>[CH:5]([N:8]([CH:15]([OH:30])[C@H:16]1[O:22][C@:20]([CH2:23][CH2:24][CH2:25][CH3:26])([OH:21])[C@H:19]([OH:27])[C@@H:18]([OH:28])[C@@H:17]1[OH:29])[C:9](=[O:14])[N:10]([CH2:11][CH2:12][Cl:13])[N:1]=[O:3])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 131714706HCID 131714706, compound

Product 1

HCID 131714705HCID 131714705, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium nitrite (0.74 g) was slowly added to a solution of 3-isopropyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (3.43 g, 8.96 mmol), obtained in the above way, in 40% aqueous acetic acid with well stirring at 0° to 5° C. After continuation of stirring for four hours at the same temperature, an ion exchange resin (13 ml, the same type as used in Example 65) was added to the resulting solution, and the mixture was stirred for 30 minutes. The ion exchange resin was filtered off, and the filtrate was vacuum-concentrated at 25° C. and purified by column chromotography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1). Thus, 2.39 g of 3-isopropyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea was obtained; yield 64.8%, m.p. 70°-72 C., [α]D20 +69.8° (C 1.0, methanol).

Workup

  1. stirringAfter continuation of stirring for four hours at the same temperature
  2. additionwas added to the resulting solution
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationThe ion exchange resin was filtered off
  5. concentrationthe filtrate was vacuum-concentrated at 25° C.
  6. custompurified by column chromotography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1)

Sources & evidence

ORD record
ord-d604636719c04c6aaf60767cf6d6aa91
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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