Methanol → HCID 69358604, compound

HRID 852586Notes

Reaction equation

HRID 852586 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([NH:9][C:10]1[C:11](F)=[C:12]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:8])=[O:7].CCN(CC)CC.[CH3:31][OH:32]>>[O:7]=[S:6]1(=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][N:9]1[C:10]1[C:11]([O:32][CH3:31])=[C:12]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 69359224HCID 69359224, compound

Product 1

HCID 69358604HCID 69358604, compoundYield 55%

Procedure

To a solution of methyl 3-{[(4-chlorobutyl)sulfonyl]amino}-2-fluoro-5-nitrobenzoate (D146) (1.5 g, 4.1 mmol, 1 equiv) in MeOH (30 ml) was added NEt3 (1.2 ml 8.6 mmol, 2.1 equiv) and the resulting solution was refluxed for 15 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with AcOEt/Et2O to give methyl 3-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-2-(methyloxy)-5-nitrobenzoate (D149) (1.2 g, 55%) as a light brown solid which was used in the next step without further purification. [M+H]+=345.1, RT2.80 min.

Workup

  1. temperaturethe resulting solution was refluxed for 15 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with a 2N aqueous HCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with AcOEt/Et2O

Sources & evidence

ORD record
ord-66a2bbd346034278a3cc66fe723bcfeb
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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