Reaction #83103

ord-5061bb5743e04cedafaf182a0c9038b8

Reaction equation

COc1ccc(CS[C@H]2CO[C@@H](COS(=O)(=O)c3ccc(C)cc3)[C@@H]2O)cc1
product
COc1ccc(CS[C@H]2CO[C@@H](COS(=O)(=O)c3ccc(C)cc3)[C@@H]2O)cc1
1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)
[Li+].[N-]=[N+]=[N-]
lithium azide
→
COc1ccc(CS[C@H]2CO[C@@H](CN=[N+]=[N-])[C@@H]2O)cc1
desired product
Yield 32.6%
COc1ccc(CS[C@H]2CO[C@@H](CN=[N+]=[N-])[C@@H]2O)cc1
1,4-Anhydro-5-azido-5-deoxy-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol
Yield 32.6%

Reactants

COc1ccc(CS[C@H]2CO[C@@H](COS(=O)(=O)c3ccc(C)cc3)[C@@H]2O)cc1
product
COc1ccc(CS[C@H]2CO[C@@H](COS(=O)(=O)c3ccc(C)cc3)[C@@H]2O)cc1
1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)
[Li+].[N-]=[N+]=[N-]
lithium azide

Reagents

None

Solvents

CN(C)C=O
N,N-dimethylformamide

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction mixture is concentrated in vacuo
  2. 2
    OtherThe residue is purified by chromatography (Silica gel: 30% ethyl acetate/hexane)

Procedure

A mixture of 2.0 g of product from Example 324, 0.460 g of lithium azide and 2 ml of N,N-dimethylformamide is stirred at 70° C. for 65 hours. The reaction mixture is concentrated in vacuo. The residue is purified by chromatography (Silica gel: 30% ethyl acetate/hexane) to give 0.454 g of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623081uspto-grants-1997_04