Sulfuric Acid → HCID 53948729, compound

HRID 2288002Notes

Reaction equation

HRID 2288002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([C:14]([OH:16])=[O:15])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:17]=[C:18]([CH3:20])[CH3:19].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O1CCOCC1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@@H:12]([C:14]([O:16][C:18]([CH3:20])([CH3:19])[CH3:17])=[O:15])[CH3:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 737465HCID 737465, compound

Product 1

HCID 53948729HCID 53948729, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[(4-fluorophenyl)sulfonyl]-D-alanine from Example 3a (8.00 g, 32.4 mmol), isobutene (120 mL), and concentrated sulfuric acid (0.5 mL) in 1,4-dioxane (20 mL) and CH2Cl2 (60 mL) was added to a 500 mL high pressure bottle and sealed. The mixture was shaken at room temperature for 95 hours at a pressure of 18 psi. The mixture was poured into an aqueous solution containing 20 g of sodium bicarbonate, which was cooled by an ice bath. The aqueous solution was extracted with ethyl acetate and the combined organic layers were washed successively with water and brine, dried with MgSO4, and concentrated to a clear, yellow oil (6.06 g). Chromatography on silica gel (20% ethyl acetate in hexane) afforded N-[(4-fluorophenyl)sulfonyl]-D-alanine, 1,1-dimethylethyl ester, as a white solid (5.00 g, 51% yield): Anal. calc'd for C13H18NO4FS: C, 51.47; H, 5.98; N, 4.62. Found: C, 51.39; H, 5.82; N, 4.53.

Workup

  1. customsealed
  2. additionThe mixture was poured into an aqueous solution
  3. temperaturewas cooled by an ice bath
  4. extractionThe aqueous solution was extracted with ethyl acetate
  5. washthe combined organic layers were washed successively with water and brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated to a clear, yellow oil (6.06 g)

Sources & evidence

ORD record
ord-491e230dac394e07ab6b756b6b1be0ff
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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