Acetic Acid → HCID 11034458, compound

HRID 1085665Notes

Reaction equation

HRID 1085665 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([OH:12])(=[O:11])[CH3:10].CN(C)C(=O)[C@H](C(C)C)[CH2:17][CH:18]=[CH:19][CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[CH2:32]1[CH2:36]OC[CH2:33]1>C1COCC1.O>[Br:1][C@H:19]([CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[C@H:18]1[O:12][C:9](=[O:11])[C@H:10]([CH:32]([CH3:36])[CH3:33])[CH2:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 54184450HCID 54184450, compound

Product 1

HCID 11034458HCID 11034458, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

88.5 g (0.5 mol) of N-bromosuccinimide and 30 g (0.5 mol) of glacial acetic acid in 1.1 liter of THF are added dropwise at 0°, over a period of 8 hours, to a solution of 60 g (0.23 mol) of 6-cyclohexyl-2(S)-isopropyl-4-hexenoic acid dimethylamide in 1.4 liters of THF/H2O (2:1). When the addition is complete, the reaction mixture is stirred for 30 minutes at 0°, then poured onto 1.8 liters of ice-cold 40% sodium hydrogen sulphite solution. The aqueous phase is extracted three times with ether and the combined organic phases are washed in succession with 1N HCl, saturated NaHCO3 solution and brine. After drying with MgSO4 and evaporating off the solvent, the residue is chromatographed over silica gel with hexane/ether (2:1) and again concentrated. The residue is recrystallised from hexane, m.p. 95°-95.5°.

Workup

  1. additionWhen the addition
  2. extractionThe aqueous phase is extracted three times with ether
  3. washthe combined organic phases are washed in succession with 1N HCl, saturated NaHCO3 solution and brine
  4. dry with materialAfter drying with MgSO4
  5. customevaporating off the solvent
  6. customthe residue is chromatographed over silica gel with hexane/ether (2:1)
  7. concentrationagain concentrated
  8. customThe residue is recrystallised from hexane, m.p. 95°-95.5°

Sources & evidence

ORD record
ord-8100f91e2c3c494fa09247b6d11154cf
Source dataset
uspto-grants-1991_04
Patent number
US05010189

Reaction notes

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