Dimethylformamide → 2,5-Anhydro-6-azido-1,3,6-trideoxy-D-ribo-hexitol

HRID 1600152Notes

Reaction equation

HRID 1600152 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C@@H:16]([CH3:17])[CH2:15][C@@H:14]2[OH:19])(=O)=O)=CC=1.CN(C)C=O.[N-:25]=[N+:26]=[N-:27].[Na+]>C(OCC)C.O.[Cl-].[Na+]>[N:25]([CH2:12][C@H:13]1[O:18][C@@H:16]([CH3:17])[CH2:15][C@@H:14]1[OH:19])=[N+:26]=[N-:27]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 867503552,5-Anhydro-1,3-dideoxy-D-ribo-hexitol 6-(4-Methylbenzenesulfonate)

Product 1

HCID 867503542,5-Anhydro-6-azido-1,3,6-trideoxy-D-ribo-hexitolYield 77.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolvent

Procedure

A mixture, under argon, of 0.560 g of product from Example 337, 2 ml of N,N-dimethylformamide and 0.250 g of sodium azide is stirred at 75°C. for 12 hours. The reaction mixture is diluted with diethyl ether, washedwith water and saturated sodium chloride, dried and concentrated in vacuo to give 0.238 g of the desired product.

Workup

  1. customdried
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfcef002dfb74ef7914735b3e5f97fe5
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

Loading…