Trifluoroacetic acid → 2-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-3-[(piperidin-4-yl)carbamoyl]pyrrolidin-3-yl]acetic acid

HRID 446020Notes

Reaction equation

HRID 446020 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:49])[CH2:14][C@@:15]1([C:33]([NH:35][CH:36]2[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]2)=[O:34])[C@H:19]([CH3:20])[CH2:18][N:17]([CH2:21][C:22]2[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:32])[CH2:16]1)(C)(C)C>ClCCl>[Cl:32][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:31])[F:30])[C:22]=1[CH2:21][N:17]1[CH2:18][C@@H:19]([CH3:20])[C@@:15]([CH2:14][C:13]([OH:49])=[O:12])([C:33](=[O:34])[NH:35][CH:36]2[CH2:37][CH2:38][NH:39][CH2:40][CH2:41]2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71293630tert-Butyl 4-[(3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate

Product 1

HCID 712937542-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-3-[(piperidin-4-yl)carbamoyl]pyrrolidin-3-yl]acetic acidYield 117.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of tert-butyl 4-[(3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate obtained in Example 5c (82 mg, 0.133 mmol) in dichloromethane (dehydrated) (3 mL) under ice-cooling, followed by stirring at room temperature for 2.5 hours. The reaction liquid was concentrated under reduced pressure, and the residue was purified by ODS column chromatography (elution solvent: water/methanol) to give the title compound (72 mg, yield: quant.).

Workup

  1. temperaturecooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was purified by ODS column chromatography (elution solvent: water/methanol)

Sources & evidence

ORD record
ord-746f9ce228c745769a397b9050987ec4
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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