Diisopropylethylamine → HCID 59819988, 화합물

HRID 563922노트

반응식

HRID 563922 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 59819988HCID 59819988, 화합물수율 84.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e2fa1dcde77e410c937eb3ef57d0f3d2
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067598B2

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