2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 86695064, compound

HRID 574328Notes

Reaction equation

HRID 574328 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:40]=[C:28]3[N:29]=[C:30]([CH3:39])[C:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])=[C:32]([Cl:33])[N:27]3[N:26]=2)[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C2[O:49]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:40]=[C:28]3[N:29]=[C:30]([CH3:39])[C:31]([CH:34]([OH:49])[C:35]([O:37][CH3:38])=[O:36])=[C:32]([Cl:33])[N:27]3[N:26]=2)[CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86695063HCID 86695063, compound

Product 1

HCID 86695064HCID 86695064, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of KHMDS (0.5 M in toluene, 1.50 mL, 0.78 mmol) in THF (12 mL) at −78° C. was added a solution of methyl 2-(2-(3-(benzyloxy)phenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.35 g, 0.83 mmol) in THF (12 mL) dropwise over 40 min. The mixture was stirred at −78° C. for 30 min. A solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (0.33 g, 1.25 mmol) in THF (24 mL) was added over 20 min and the reaction mixture was stirred for additional 30 min at −78° C. The reaction mixture was quenched with saturated NH4Cl aqueous solution (2 mL). The reaction mixture was allowed to warm to room temperature and then diluted with ethyl acetate (100 mL). The organic phase was washed with water and brine and dried with sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (80 mg, 22%). Used as is in the next step.

Workup

  1. stirringthe reaction mixture was stirred for additional 30 min at −78° C
  2. customThe reaction mixture was quenched with saturated NH4Cl aqueous solution (2 mL)
  3. temperatureto warm to room temperature
  4. additiondiluted with ethyl acetate (100 mL)
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was evaporated
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-29e90067c5b44e8682ba38da3363d5d8
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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