Potassium nitrite → HCID 131714697, compound

HRID 1981662Notes

Reaction equation

HRID 1981662 reaction equation
[N:1]([O-:3])=O.[K+].[CH3:5][O:6][C:7]1[CH:36]=[CH:35][C:10]([CH2:11][N:12]([CH:19]([OH:34])[C@H:20]2[O:26][C@:24]([CH2:27][CH2:28][CH2:29][CH3:30])([OH:25])[C@H:23]([OH:31])[C@@H:22]([OH:32])[C@@H:21]2[OH:33])[C:13](=[O:18])[NH:14][CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1>O1CCCC1.Cl>[CH3:5][O:6][C:7]1[CH:36]=[CH:35][C:10]([CH2:11][N:12]([CH:19]([OH:34])[C@H:20]2[O:26][C@:24]([CH2:27][CH2:28][CH2:29][CH3:30])([OH:25])[C@H:23]([OH:31])[C@@H:22]([OH:32])[C@@H:21]2[OH:33])[C:13](=[O:18])[N:14]([CH2:15][CH2:16][Cl:17])[N:1]=[O:3])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 516910Potassium nitriteHCID 131714698HCID 131714698, compound

Product 1

HCID 131714697HCID 131714697, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium nitrite (2 g) was added at 0° to 5° C. to a solution of the above synthesized 3-(p-methoxybenzyl)-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (3.85 g, 8.35 mmol) in a mixture of tetrahydrofuran (100 ml) and 10% hydrochloric acid (10 ml). After stirring at the same temperature for 10 minutes, the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, vacuum-concentrated at 25° C., and purified by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1). Thus, 2.35 g of 3-(p-methoxybenzyl)-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea was obtained; yield 57.4%, m.p. 86°-88° C., [α]D20 +61.5° (C 1.0, methanol).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationvacuum-concentrated at 25° C.
  4. custompurified by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1)

Sources & evidence

ORD record
ord-952103abe1534665a09c6983cf74baf2
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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