Trifluoroacetic acid → HCID 68771453, compound

HRID 1171607Notes

Reaction equation

HRID 1171607 reaction equation
[CH:1]([S:4]([CH2:7][C@H:8]1[C@@H:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:15]2=[O:32])[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1)(=[O:6])=[O:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]([S:4]([CH2:7][C@H:8]1[C@@H:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=3)[C:15]2=[O:32])[CH2:12][CH2:11][NH:10][CH2:9]1)(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68765620HCID 68765620, compound

Product 1

HCID 68771453HCID 68771453, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A sample of (3R,4S)-tert-butyl 3-(isopropylsulfonylmethyl)-4-((S)-2-oxo-3-(3-(trifluoromethyl)benzamido)pyrrolidin-1-yl)piperidine-1-carboxylate (0.688 g) was dissolved in CH2Cl2 (10 mL) prior to the addition of trifluoroacetic acid (0.92 mL, 11.9 mMol). After 4 h, the reaction was made basic with saturated NaHCO3. Extracted with CH2Cl2. The organic layer was washed with brine and dried (MgSO4). Concentrated and dried in vacuo to yield the desired product, N—((S)-1-((3R,4S)-3-(isopropylsulfonylmethyl)piperidin-4-yl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide) (0.482 g, yield=85%). MS found: (M+H)+=476.31.

Workup

  1. extractionExtracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationConcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a59935ab22974fa0bc872d854919e980
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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