Hexane → HCID 131714695, compound

HRID 1981661Notes

Reaction equation

HRID 1981661 reaction equation
C([O-])(=O)C.[Na+].[CH:6]1([CH2:12][N:13]([C@:20]2([OH:35])[C@H:26]([OH:27])[C@@H:25]([CH2:28][OH:29])[O:24][C@:22]([CH2:30][CH2:31][CH2:32][CH3:33])([OH:23])[C@@H:21]2[OH:34])[C:14](=[O:19])[NH:15][CH2:16][CH2:17][Cl:18])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[N+:36]([O-])([N+]([O-])=O)=[O:37].CCCCCC>O1CCCC1.C(O)(=O)C>[CH:6]1([CH2:12][N:13]([C@:20]2([OH:35])[C@H:26]([OH:27])[C@@H:25]([CH2:28][OH:29])[O:24][C@:22]([CH2:30][CH2:31][CH2:32][CH3:33])([OH:23])[C@@H:21]2[OH:34])[C:14](=[O:19])[N:15]([CH2:16][CH2:17][Cl:18])[N:36]=[O:37])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 25352Nitrogen oxide (N2O4)HCID 517045Sodium AcetateHCID 131714696HCID 131714696, compound

Product 1

HCID 131714695HCID 131714695, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous sodium acetate (15 g) was added to a solution of 3-cyclohexylmethyl-3-(n-butyl α-D-glucopyranose-3-yl)-1-(2-chloroethyl)urea (3.94 g, 9.02 mmol) in a mixture of tetrahydrofuran (120 ml) and acetic acid (20 ml), and dinitrogen tetraoxide gas (4 g) was introduced into the mixture with well stirring at 0° to 5° C. spending 5 minutes. After the mixture was stirred at the same temperature for further 30 minutes to complete reaction, n-hexane (200 ml) was added and insoluble matter was filtered off. The filtrate was vacuum-concentrated at 25° C. and fractionated by column chromatography (packing: silica gel; eluent: ethyl acetate/chloroform/methanol (2:10:1) to isolate the objective product. Thus, 1.62 g of 3-cyclohexylmethyl-3-(n-butyl α-D-glucopyranose-3-yl)-1-(2-chloroethyl)-1-nitrosourea was obtained; yield 38.5%, m.p. 75°-77° C., [α]D20 +47.2° (C 1.0, methanol).

Workup

  1. additionwas introduced into the mixture
  2. additionwas added
  3. filtrationinsoluble matter was filtered off
  4. concentrationThe filtrate was vacuum-concentrated at 25° C. and fractionated by column chromatography (packing
  5. customeluent: ethyl acetate/chloroform/methanol (2:10:1) to isolate the objective product

Sources & evidence

ORD record
ord-f2558a0f0d1b4b5dbaf30b7c7799b592
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

Loading…