2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 77561083, compound

HRID 1454347Notes

Reaction equation

HRID 1454347 reaction equation
[Na].[CH2:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:19]2)=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:34])C=CC=CC=1>C1COCC1>[CH3:26][O:25][C:23]([C:20]1([OH:34])[CH2:21][CH2:22][N:18]([CH2:17][C:14]2[CH:13]=[CH:12][C:11]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:16][CH:15]=2)[CH2:19]1)=[O:24]

Participants

5

Reactant 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 5360545SodiumHCID 85850741HCID 85850741, compound

Product 1

HCID 77561083HCID 77561083, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-72 °C

Procedure

To a solution of 0.52 mL (0.52 mmol) of 1.0M sodium hexamethylsilazide in THF at −78° C. was added 153 mg (0.44 mmol) of (R/S)-1-(4-nonylphenyl)methyl-pyrrolidin-3-yl carboxylic acid, methyl ester (from EXAMPLE 34, Step C) in 1 mL of THF while maintaining the internal temperature at less −72° C. After 20 min, 172 mg (0.65 mmol) of 2-(phenylsulfonyl)-3-phenyloxaziridine (Davis Reagent) in 1 mL of THF was added while maintaining the internal temperature at less −69° C. After stirring for 1.25 h at −78° C., the reaction was quenched with 1N NaHCO3 and warmed to rt. After removing volatiles under reduced pressure, the reaction mixture was diluted with 50 mL of 1N NaHCO3 and 50 mL of sat'd NaCl. The aqueous phase was extracted with 3×50 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 4:1 v/v hexane/EtOAc and 4:1 v/v hexane/acetone as the gradient to afford 11 mg (7%) of the title compound as a colorless film: RF: 0.39 (4:1 v/v hexane/acetone); 1H-NMR (500 MHz) δ 0.90 (t, J=6.8, 3H), 1.28-1.33 (m, 12H), 1.59-1.64 (m, 2H), 2.02 (m, 1H), 2.42 (m, 1H), 2.60 (t, J=7.8, 2H), 2.67 (m, 1H), 2.86 (ABq, J=10.1, 2H), 2.97 (m, 1H), 3.69 (s, 2H), 3.82 (s, 3H), 7.14 (d, J=7.9, 2H), 7.26 (d, J=7.9, 2H).

Workup

  1. temperaturewhile maintaining the internal temperature at less −69° C
  2. customthe reaction was quenched with 1N NaHCO3
  3. temperaturewarmed to rt
  4. customAfter removing volatiles under reduced pressure
  5. additionthe reaction mixture was diluted with 50 mL of 1N NaHCO3 and 50 mL of sat'd NaCl
  6. extractionThe aqueous phase was extracted with 3×50 mL of CH2Cl2
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d613ac476d0a4cd0a1052aa056543f44
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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