Diisopropylethylamine → HCID 59819988, compound

HRID 563922Notes

Reaction equation

HRID 563922 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:47][C:48]1[S:52][C:51]([CH2:53][CH2:54][NH2:55])=[CH:50][CH:49]=1>CN(C=O)C>[CH3:47][C:48]1[S:52][C:51]([CH2:53][CH2:54][NH:55][C:9](=[O:11])[CH2:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=2)=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 35887363-(4-(Trifluoromethyl)phenyl)propionic AcidHCID 147881892-(5-Methylthiophen-2-yl)ethan-1-amine

Product 1

HCID 59819988HCID 59819988, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3 g (13 mmol) 4-(trifluoromethyl)hydrocinnamic acid (commercially available) in 30 mL DMF under argon were added 4.7 g (14.37 mmol) TBTU and 11.2 mL (65.3 mmol) N-ethyldiisopropylamine. A solution of 1.85 g (13 mmol) 2-(5-methyl-thiophen-2-yl)-ethylamine in 5 mL DMF was added drop wise over a period of 2 minutes. The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with water and with a sat. NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo. The solid was stirred in 30 mL ether, filtered and dried. The mother liquor was concentrated in vacuo and purified on silica eluting with a gradient formed from heptane and ethyl acetate. The product containing fractions were evaporated. 3.75 g (84%) of the title compound was yielded as white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with water and with a sat. NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. stirringThe solid was stirred in 30 mL ether
  8. filtrationfiltered
  9. customdried
  10. concentrationThe mother liquor was concentrated in vacuo
  11. custompurified on silica eluting with a gradient
  12. customformed from heptane and ethyl acetate
  13. additionThe product containing fractions
  14. customwere evaporated

Sources & evidence

ORD record
ord-e2fa1dcde77e410c937eb3ef57d0f3d2
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

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