2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 11462211, compound

HRID 1271954Notes

Reaction equation

HRID 1271954 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[CH:7]=1)=[O:5])[CH3:2].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:31])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:31])[N:12]=[CH:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 69208485HCID 69208485, compound

Product 1

HCID 11462211HCID 11462211, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1.2 g, 3.6 mmol) was dissolved in CH2Cl2 (20 mL) and treated with 2-benzenesulfonyl-3-phenyl-oxaziridine (1.13 g, 4.32 mmol) at room temperature and stirred for 1 day. Following concentration under reduced pressure, the crude reaction mixture was chromatographed on silica gel eluting with ethyl acetate to give 8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a white solid (0.85 g, 68%). MS (APCI); M++1: Calc'd, 350.1, Found 350.0.

Workup

  1. concentrationconcentration under reduced pressure
  2. customthe crude reaction mixture
  3. customwas chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-256ddaffbb2d4c43bf738a0204586aa2
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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