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

HRID 1290365Notes

Reaction equation

HRID 1290365 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-d73c3b7ef6c0444da33e3e284a54f9e3
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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