Ammonium Chloride → HCID 18931032, compound

HRID 1598958Notes

Reaction equation

HRID 1598958 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C2[O:36]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1.[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH:8]([OH:36])[C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 18931034HCID 18931034, compound

Product 1

HCID 18931032HCID 18931032, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the title compound of Step C (0.73 g, 2.92 mmol) in anhydrous THF (10 mL) at -78° C. under N2 was added potassium bis(trimethylsilyl)amide (6.43 mL of a 0.5M solution in toluene, 3.22 mmol). After 10 min, a solution of 3-phenyl-2-(phenylsulfonyl)oxaziridine (1.14 g, 4.38 mmol) in THF (10 mL) was added via syringe causing the brown solution to turn yellow. After 20 min, 10% aqueous NH4Cl was added and the aqueous layer was extracted with ether (2×60 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to an oily solid. This solid was triturated with hexanes and filtered off. Purification of the filtrate by column chromatography eluting with 4-25% ethyl acetate/hexanes afforded the title compound of Step D as a colorless oil (0.29 g). 1H NMR (CDCl3, 300 MHz) δ8.36 (dd, 1H), 7.9-8.1 (m,2H), 7.51 (m, 1H), 7.22 (m, 1H), 7.05-7.18 (m,2H), 6.32 (m, 1H), 4.21 (br s, 1H). APCI+ found 266 (M+1); calc 265 (M).

Workup

  1. waitAfter 20 min
  2. extractionthe aqueous layer was extracted with ether (2×60 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo to an oily solid
  5. customThis solid was triturated with hexanes
  6. filtrationfiltered off
  7. customPurification of the filtrate by column chromatography
  8. washeluting with 4-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f3037f91867d4b5b8eca75df61f5d096
Source dataset
uspto-grants-1998_04
Patent number
US05739326

Reaction notes

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