Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 131730571, compound

HRID 2093054Notes

Reaction equation

HRID 2093054 reaction equation
[C:1]([N:8]1[CH2:13]CC(=O)C(Br)C1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[O:18][C:19]([C:21]([NH2:23])=S)=[O:20].[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O-])(=O)=O)=[CH:27]C=1.C1C=C[NH+]=CC=1>C1(C)C=CC=CC=1.O>[C:1]([N:8]1[C:29]2[CH2:30][CH2:25][NH:23][CH2:27][C:28]=2[S:31][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:24][CH2:21][C:19]([O-:18])=[O:20]

Participants

6

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 2733398Ethyl thiooxamateHCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

Product 1

HCID 131730571HCID 131730571, compoundYield 317%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

N-boc-3-bromo-4-piperidone (110 gm, 0.395 mole) obtained in step IV was dissolved in 500 ml of dry toluene. Ethyl thioxamate (68.4 g, 0.514 mole) obtained in step II and PPTS (10 gm, 0.039 mole) were added to toluene solution. Mixture was refluxed azeotropically for 8 h, followed by concentration. The residue obtained was taken in water and extracted with dichloromethane. The organic layer was washed with water, brine and dried over anhydrous sodium sulphate and concentrated. Residue obtained was purified by column chromatography using 1% MeOH/CH2Cl2 as eluent to get the 39.0 gm of N-boc-4,5,6,7-tetrahydrothiazolo-[5,4-c]-pyridine-2-ethylcarboxylate.

Workup

  1. temperatureMixture was refluxed azeotropically for 8 h
  2. concentrationfollowed by concentration
  3. customThe residue obtained
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. customResidue obtained
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-aa50f560ece44ff6b9ad91f492979fa9
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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