Trichloroacetonitrile → HCID 86685888, Verbindung

HRID 1629794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629794
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([OH:15])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(C#N)(Cl)(Cl)Cl.[NH2:41][C@@:42]([C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][C:67]([F:70])([F:69])[F:68])=[CH:59][CH:58]=1)([C:53]([F:56])([F:55])[F:54])[CH2:43][C:44]([C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=1)=[O:45]>C(Cl)Cl.N1C=CC=CC=1>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]([NH:41][C@:42]([C:57]1[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][C:67]([F:68])([F:69])[F:70])=[CH:59][CH:58]=1)([CH2:43][C:44](=[O:45])[C:46]1[CH:47]=[CH:48][C:49]([CH3:52])=[CH:50][CH:51]=1)[C:53]([F:56])([F:55])[F:54])=[O:15]

Komponenten

7

Edukt 4

HCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 20825N-PhthaloylglycineHCID 86685849(S)-3-Amino-4,4,4-trifluoro-1-p-tolyl-3-(4-(4,4,4-trifluorobutoxy)phenyl)-butan-1-one

Produkt 1

HCID 86685888HCID 86685888, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of 2-(1,3-dioxoisoindolin-2-yl)acetic acid (592 mg, 2.88 mmol) in dry DCM (10 mL) was added PPh3 (2269 mg, 8.65 mmol) fairy rapidly, and then CCl3CN (500 mg, 3.46 mmol) was added dropwise. The mixture was stirred at rt for 3 h and a solution of Intermediate 2F, isomer 2 (500 mg, 1.15 mmol) in dry DCM (3 mL), followed by pyridine (0.3 mL) were added. The mixture was stirred at rt overnight. The mixture was diluted with DCM (10 mL) and washed with sat'd NaHCO3 (2×8 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography to yield the desired product (620 mg, 87%). LCMS Anal. Calc'd for C31H26F6N2O5 620.17, found [M+H] 621.3.

Aufarbeitung

  1. additionwere added
  2. stirringThe mixture was stirred at rt overnight
  3. washwashed with sat'd NaHCO3 (2×8 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5dd3dbb87b6a447099c954a5be7eb6ad
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791091B2

Notizen zur Reaktion

Wird geladen…