Trifluoroacetic acid → HCID 58779093, compound

HRID 1372590Notes

Reaction equation

HRID 1372590 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][C@@H:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][C@H:16]1[CH2:27][O:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)=O)(C)(C)C>C(Cl)Cl>[O:20]([C@@H:18]1[CH2:19][NH:15][C@H:16]([CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=2)[CH2:17]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67405696HCID 67405696, compound

Product 1

HCID 58779093HCID 58779093, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml) was added to a solution of methyl 4-((2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylmethoxy)benzoate (2.02 g, 3.25 mmol) in methylene chloride (100 ml). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was then concentrated under reduced pressure. The residue was diluted with methylene chloride (50 ml), followed by washing with 1N NaOH. The organic layer was fractionated, followed by washing with saturated brine, drying over anhydrous sodium sulfate and distillation under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 70 g), whereby from chloroform/acetone (10/1) chloroform/methanol (10/1) eluate fractions, the title compound (970 mg, 91%) was obtained as a brown oil.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionThe residue was diluted with methylene chloride (50 ml)
  3. washby washing with 1N NaOH
  4. washby washing with saturated brine
  5. dry with materialdrying over anhydrous sodium sulfate and distillation under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (silica gel: 70 g), whereby from chloroform/acetone (10/1) chloroform/methanol (10/1) eluate fractions

Sources & evidence

ORD record
ord-22264142f7734a9b8f2d1cc435bb57e1
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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