Trifluoroacetic acid → HCID 68767705, compound

HRID 1455473Notes

Reaction equation

HRID 1455473 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].F[C:41](F)(F)[C:42](O)=O.[C:47]([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:41]([N:10]1[CH2:11][CH2:12][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:29])([F:28])[F:30])[CH:22]=3)[C:15]2=[O:32])[C@H:8]([CH2:7][S:4]([CH:1]([CH3:3])[CH3:2])(=[O:5])=[O:6])[CH2:9]1)([CH3:42])[CH3:47].[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

6

Reactant 3

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

Product 2

HCID 68767705HCID 68767705, compoundHCID 68771453HCID 68771453, compound

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-670622b67b284f159791353c23bc9471
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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