Sulfuric Acid → HCID 18665866, compound

HRID 1458959Notes

Reaction equation

HRID 1458959 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@@H:11]([CH2:15][NH2:16])[C:12]([OH:14])=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:18][C:19](=[CH2:21])[CH3:20].OS(O)(=O)=O>O1CCOCC1.C(OCC)(=O)C>[C:19]([C@:11]([NH:10][S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:17])=[CH:6][CH:5]=1)(=[O:8])=[O:9])([CH2:15][NH2:16])[C:12]([OH:14])=[O:13])([CH3:21])([CH3:20])[CH3:18]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 15589163-Amino-N-((4-methylphenyl)sulfonyl)-L-alanine

Product 1

HCID 18665866HCID 18665866, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Acid 14-3 (5.0 g, 19.4 mmol) was suspended in dioxane (100 ml) in a 1-L pressure bottle. The bottle was cooled to -15° and isobutylene (100 ml) was condenced into the dioxane. Concentrated H2SO4 (5 ml) was added and the bottle sealed and stirred at room temperature for 36 h. The bottle was opened and the excess isobutylene carefully vented. The solution was diluted with ethyl acetate (200 ml) and washed with 1N NaOH (200 ml). The organic layer was dried (Na2SO4), filtered and evaporated to give 14-4 as a white crystaline solid.

Workup

  1. temperatureThe bottle was cooled to -15°
  2. customthe bottle sealed
  3. washwashed with 1N NaOH (200 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d9c11910bde24468b91c41bc4a618711
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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