Trifluoroacetic acid → (3S)-3-Amino-1-methyl-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-2-one

HRID 626881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626881
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:13][CH2:12][C@@:11]([NH:33]C(=O)OC(C)(C)C)([CH2:14][C:15]#[C:16][C:17]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=2)[C:10]1=[O:41]>ClCCl>[NH2:33][C@@:11]1([CH2:14][C:15]#[C:16][C:17]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=2)[CH2:12][CH2:13][N:9]([CH3:8])[C:10]1=[O:41]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 90015348tert-Butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-3-yl]carbamate

Produkt 1

HCID 90015136(3S)-3-Amino-1-methyl-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-2-oneAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (2 mL, 26.9 mmol) was added to a solution of tert-butyl N-[(3S)-1-methyl-2-oxo-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-3-yl]carbamate (which may be prepared as described in Description 7) (555 mg, 1.17 mmol) in dichloromethane (10 mL) at 20° C. and the reaction was stirred for 1 hr. The reaction was quenched by the addition of sat. NaHCO3 and the phases were separated. The organic layer was dried (Na2SO4) and the solvent evaporated to afford the (3S)-3-amino-1-methyl-3-[3-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]prop-2-ynyl]pyrrolidin-2-one (D8) (340 mg, 0.9082 mmol, 77.6% yield) as a yellow oil.

Aufarbeitung

  1. customThe reaction was quenched by the addition of sat. NaHCO3
  2. customthe phases were separated
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4c17711eaa2343438da946c082605fd7
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309254B2

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