2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 11291449, compound

HRID 272441Notes

Reaction equation

HRID 272441 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:17](=[O:18])[N:16]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:9]2[N:10]=[C:11]([S:14][CH3:15])[N:12]=[CH:13][C:8]=2[C:7]=1[CH3:24])=[O:5])[CH3:2].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:32])C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:17](=[O:18])[N:16]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:9]2[N:10]=[C:11]([S:14]([CH3:15])=[O:32])[N:12]=[CH:13][C:8]=2[C:7]=1[CH3:24])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 11233308HCID 11233308, compound

Product 1

HCID 11291449HCID 11291449, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-cyclopentyl-5-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (138 mg, 0.40 mmol) was dissolved in CH2Cl2 (6 mL) and 2-benzenesulfonyl-3-phenyl-oxaziridine (155 mg, 0.6 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours then the solvent was removed under reduced pressure and the remaining residue was purified by prepative TLC (50% ethyl acetate/hexane). The more polar, product-containing, reaction was extracted into CH2Cl2 and the solvent evaporated to provide 8-cyclopentyl-2-methanesulfinyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a white solid (110 mg, 75.7%). M++1: Calc'd. 364.4. Found 364.2.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe remaining residue was purified by prepative TLC (50% ethyl acetate/hexane)
  3. additionThe more polar, product-containing
  4. customreaction
  5. extractionwas extracted into CH2Cl2
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-11944d1a54104e75ab1d59017be93136
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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