Methyl 3-[4-(azetidine-1-carbonyl)-2-chloro-phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate → Methyl 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate

HRID 600541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600541
[N:1]1([C:5]([C:7]2[CH:31]=[CH:30][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])[CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])=[C:9](Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1>[Pd].C1COCC1.C(O)C>[N:1]1([C:5]([C:7]2[CH:31]=[CH:30][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])[CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 1

HCID 59761167Methyl 3-[4-(azetidine-1-carbonyl)-2-chloro-phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate2×

Produkt 1

HCID 59761134Methyl 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 3-[4-(azetidine-1-carbonyl)-2-chloro-phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 17) (372 mg, 0.81 mmol) was added to a suspension of 10% palladium on carbon (37 mg, catalytic) in THF (10 mL) and ethanol (10 mL) and the resulting mixture was stirred under an atmosphere of hydrogen for 16 hours. The suspension was filtered and the filtrate evaporated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), washed with water (10 mL) and brine (10 mL), dried (MgSO4) and evaporated under reduced pressure to afford the product (309 mg, 90%). 1HNMR δ (300 MHz, CDCl3) 2.10-2.23 (m, 1H), 2.36 (quintet, 2H), 2.52-2.65 (m, 1H), 2.94 (s, 3H), 3.32-3.54 (m, 2H), 3.89 (s, 3H), 4.18-4.39 (m, 4H), 4.90 (t, 1H), 6.94 (s, 1H), 7.01 (d, 2H), 7.32 (s, 1H), 7.48 (s, 1H), 7.64 (d, 2H); m/z 425 (M+H)+

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  4. washwashed with water (10 mL) and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-584d3d5b14d04c30816f356996a209bc
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902200B2

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