2-Mercaptobenzoic Acid → HCID 68951149, compound

HRID 238992Notes

Reaction equation

HRID 238992 reaction equation
C1(P(C2C=CC=CC=2)CCC(P(C2C=CC=CC=2)C2C=CC=CC=2)C)C=CC=CC=1.C([N:34]1[CH2:38][CH2:37][C@@H:36]([C:39]2[CH:44]=[CH:43][C:42]([NH:45][S:46]([C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:58])([F:57])[F:56])[CH:50]=3)(=[O:48])=[O:47])=[CH:41][CH:40]=2)[CH2:35]1)C=C.SC1C=CC=CC=1C(O)=O>O1CCCC1>[NH:34]1[CH2:38][CH2:37][C@@H:36]([C:39]2[CH:44]=[CH:43][C:42]([NH:45][S:46]([C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:58])([F:56])[F:57])[CH:50]=3)(=[O:48])=[O:47])=[CH:41][CH:40]=2)[CH2:35]1

Participants

5

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 23414403HCID 23414403, compoundHCID 68950383HCID 68950383, compound

Product 1

HCID 68951149HCID 68951149, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.071 g of tris-(dibenzylidenaceton)-dipalladium(0) (0.08 mmol) and 0.033 g of 1,3-bis-(diphenylphosphino)-butane (0.08 mmol) were dissolved in 20 ml tetrahydrofurane and stirred for 30 min. 0.32 g of N-[4-((S)-1-allyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethyl-benzenesulfonamide (0.78 mmol), dissolved in 5 ml tetrahydrofurane, were added to the solution, followed by 0.129 g 2-mercaptobenzoic acid (0.84 mmol). The reaction mixture was stirred at room temperature for 72 h, the solvent was evaporated, and dichloromethane and 1 N aqueous hydrochloric acid were added. The aqueous phase was adjusted to basic pH, extracted with dichlormethane and the combined organic layers were washed with aqueous sodium chloride solution, dried over sodium sulphate, filtered and evaporated to dryness under reduced pressure. The crude product was purified via silica gel chromatography using a ISCO companion instrument to yield 0.01 g of product.

Workup

  1. additionwere added to the solution
  2. stirringThe reaction mixture was stirred at room temperature for 72 h
  3. customthe solvent was evaporated
  4. additiondichloromethane and 1 N aqueous hydrochloric acid were added
  5. extractionextracted with dichlormethane
  6. washthe combined organic layers were washed with aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure
  10. customThe crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-cf6bcb019d1c4892a125bae3369a0be1
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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