p-Toluenesulfonic acid → 7-[(1-Ethoxyethoxy)methyl]-7,8-dihydro-5H-[1,4]oxazino[4,3-b]thieno[3,2-e]-1,2-thiazine-5-one 10,10-dioxide

HRID 1490053Notes

Reaction equation

HRID 1490053 reaction equation
[OH:1][CH2:2][CH:3]1[O:12][C:11](=[O:13])[C:10]2[N:5]([S:6](=[O:18])(=[O:17])[C:7]3[S:16][CH:15]=[CH:14][C:8]=3[CH:9]=2)[CH2:4]1.[CH:19]([O:21][CH2:22][CH3:23])=[CH2:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH2:19]([O:21][CH:22]([O:1][CH2:2][CH:3]1[O:12][C:11](=[O:13])[C:10]2[N:5]([S:6](=[O:17])(=[O:18])[C:7]3[S:16][CH:15]=[CH:14][C:8]=3[CH:9]=2)[CH2:4]1)[CH3:23])[CH3:20]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 214805027-Hydroxymethyl-7,8-dihydro-5H-[1,4]oxazino[4,3-b]thieno[3,2-e]-1,2-thiazine-5-one 10,10-dioxide

Product 1

HCID 214804957-[(1-Ethoxyethoxy)methyl]-7,8-dihydro-5H-[1,4]oxazino[4,3-b]thieno[3,2-e]-1,2-thiazine-5-one 10,10-dioxideYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the product from Step C (10 g, 34.84 mmol) in anhydrous THF (200 mL) at 0° C. was combined with ethyl vinyl ether (5.02 g, 69.68 mmol) and p-toluenesulfonic acid (1.32 g, 6.9 mmol); this mixture was stirred until it became homogeneous. The reaction mixture was filtered through silica and the solvent evaporated to give a residue which was purified by column chromatography (silica, ethyl acetate/hexane, 3:7) to give 6.8 g (54%) of an oil.

Workup

  1. filtrationThe reaction mixture was filtered through silica
  2. customthe solvent evaporated
  3. customto give a residue which
  4. customwas purified by column chromatography (silica, ethyl acetate/hexane, 3:7)

Sources & evidence

ORD record
ord-d01c1dbd12f84cd4aeb2762212461a4d
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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