1-Butanaminium, N,N,N-tributyl-, azide → Ethanethioic acid trans-(+/-)S-[5-(azidomethyl)tetrahydro-3-furanyl]ester

HRID 1600098Notes

Reaction equation

HRID 1600098 reaction equation
FC(F)(F)S(O[CH2:7][C@@H:8]1[O:12][CH2:11][C@@H:10]([S:13][C:14](=[O:16])[CH3:15])[CH2:9]1)(=O)=O.[N-:19]=[N+:20]=[N-:21].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[N:19]([CH2:7][C@@H:8]1[O:12][CH2:11][C@@H:10]([S:13][C:14](=[O:16])[CH3:15])[CH2:9]1)=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 86750748Ethanethioic acid trans(+/-)-S-[tetrahydro-5-[[[(trifluoromethyl)sulfonyl]oxy]methyl]-3-furanyl]ester

Product 1

HCID 86750322Ethanethioic acid trans-(+/-)S-[5-(azidomethyl)tetrahydro-3-furanyl]esterYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 5.768 g of product from Example 22 in 16 ml of methylene chloride, under argon, is added, via syringe, a 0° C. solution of 5.86 g of tetrabutylammonium azide in 16 ml of methylene chloride. The reaction is stirred in an ice bath for 30 minutes and then concentrated in vacuo. The residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane) to give 3.418 g of the desired product.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-144eb0c9731f4b39b8b2cb37c4cc9116
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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