Sulfoxonium, trimethyl-, iodide (1:1) → HCID 86622359, compound

HRID 501746Notes

Reaction equation

HRID 501746 reaction equation
[I-].C[S+](C)(C)=O.CC(C)([O-])C.[K+].[CH2:13]([O:20][C:21]([NH:23][C@@H:24]([CH2:37][C:38]1[CH:43]=[C:42]([Cl:44])[CH:41]=[C:40]([Cl:45])[CH:39]=1)[C:25]([O:27][C:28]1C=CC([N+]([O-])=O)=CC=1)=O)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[Cl:44][C:42]1[CH:43]=[C:38]([CH2:37][C@H:24]([NH:23][C:21](=[O:22])[O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:25]2[CH2:28][O:27]2)[CH:39]=[C:40]([Cl:45])[CH:41]=1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 68465085HCID 68465085, compound

Product 1

HCID 86622359HCID 86622359, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Step BF (4): To a mixture of trimethylsulfoxonium iodide (20.72 g, 94.2 mmol) in THF (175 mL) was added solid potassium t-butoxide (8.792 g, 78.7 mmol) and the mixture was refluxed for 3 h. The mixture was cooled to 0° C., to which a solution of (S)-4-nitrophenyl 2-(benzyloxycarbonylamino)-3-(3,5-dichlorophenyl)propanoate (15.35 g, 31.40 mmol) in THF (70 mL) was added. The mixture was brought to rt, and stirred for 16 h. Solvents were removed in vacuo. Water and EtOAc were then added, and the solid material filtered (Buchner funnel). The yellowish solid was washed with water and hexane until a white solid remained. The solid was dried in a vacuum oven. All liquid layers were combined and extracted 3 times to EtOAc. The combined organic layers were back-extracted with dilute NaOH, washed with brine, dried over MgSO4, and concentrated in vacuo. The combined material was the desired compound (13.40 g, 97% yield). 1H NMR (500 MHz, CDCl3) δ 6.99-7.39 (m, 8H) 5.80 (d, J=7.93 Hz, 1H) 5.01-5.15 (m, 2H) 4.25-4.37 (m, 2H) 3.31 (s, 3H) 3.26 (s, 3H) 2.96 (d, J=6.41 Hz, 2H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. additionwas added
  3. customwas brought to rt
  4. customSolvents were removed in vacuo
  5. additionWater and EtOAc were then added
  6. filtrationthe solid material filtered (Buchner funnel)
  7. washThe yellowish solid was washed with water and hexane until a white solid
  8. customThe solid was dried in a vacuum oven
  9. extractionextracted 3 times to EtOAc
  10. extractionThe combined organic layers were back-extracted with dilute NaOH
  11. washwashed with brine
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5c93ccc27a349ffa751b9b4a13f3b3f
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

Loading…