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

HRID 54826Notes

Reaction equation

HRID 54826 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>[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

5

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 1

HCID 3283Diethyl EtherSolvent

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, washed with water and saturated sodium chloride, dried and concentrated in vacuo to give 0.238 g of the desired product.

Workup

  1. washwashed with water and saturated sodium chloride
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65cba0136c614283a20f8a7670d3a412
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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