2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 11188518, compound

HRID 272421Notes

Reaction equation

HRID 272421 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[C:19](=[O:20])[N:18]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:34])C=CC=CC=1>ClCCl.CO>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[C:19](=[O:20])[N:18]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:11]2[N:12]=[C:13]([S:16]([CH3:17])=[O:34])[N:14]=[CH:15][C:10]=2[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 11199740HCID 11199740, compound

Product 1

HCID 11188518HCID 11188518, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
25 °C

Procedure

(8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-carbamic acid tert-butyl ester (1.3 g, 3.45 mmol, prepared according to Example 8) was added to 50:50 dichloromethane/methanol (12 ml) followed by 2-benzenesulfonyl-3-phenyl-oxaziridine (1.08 g, 4.14 mmol). The mixture was stirred at 25° C. for 3.5 hours, evaporated to an oil and eluted through silica gel with chloroform. Fractions containing the product were evaporated to yield (8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-carbamic acid tert-butyl ester as a solid (1.2 g, 89%). MS (APCI); M++1: Calc'd, 393.15. Found 393.1.

Workup

  1. customevaporated to an oil
  2. washeluted through silica gel with chloroform
  3. additionFractions containing the product
  4. customwere evaporated

Sources & evidence

ORD record
ord-8cebc20c0bb84b0888727a4a044289fa
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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