2-(Trifluoromethyl)benzoic acid → HCID 57748835, compound

HRID 598516Notes

Reaction equation

HRID 598516 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)(C)(C)C.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.OS([O-])(=O)=O.[K+]>CN(C=O)C>[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:18]([C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=2[C:15]([F:14])([F:25])[F:26])=[O:19])[CH2:9]1

Participants

7

Reactant 5

HCID 98992-(Trifluoromethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 57748835HCID 57748835, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.363 g (1.95 mmol) (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (commercially available), 0.38 g (2 mmol) 2-trifluoromethyl-benzoic acid (commercially available), 0.69 g (2.15 mmol) TBTU and 0.378 g (2.92 mmol) DIPEA in 8 mL DMF was stirred at room temperature for 16 h. KHSO4 aq. was added and the mixture was extracted with ethyl acetate. The combined organic layers were evaporated and the residue was treated with 4.87 mL 4N HCl in dioxane and stirred for 16 h at room temperature. The mixture was concentrated and methanol and water was added and the mixture was passed over a basic solid phase extraction cartridge eluting with methanol. The title compound was obtained after evaporation and used without further purification in the consecutive step. (MH+) 259.1.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe combined organic layers were evaporated
  3. additionthe residue was treated with 4.87 mL 4N HCl in dioxane
  4. stirringstirred for 16 h at room temperature
  5. concentrationThe mixture was concentrated
  6. additionmethanol and water was added
  7. extractionthe mixture was passed over a basic solid phase extraction cartridge
  8. washeluting with methanol

Sources & evidence

ORD record
ord-36c4b1c737a541d49472f438501d726e
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

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