Cyclopentylacetic acid → HCID 86714411, Verbindung

HRID 1750198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750198
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[C:34]([NH2:44])[CH:33]=1>CN(C=O)C.O.C(Cl)CCl>[CH3:29][O:30][C:31](=[O:45])[C:32]1[CH:37]=[CH:36][C:35]([NH:38][CH:39]([CH2:40][CH3:41])[CH2:42][CH3:43])=[C:34]([NH:44][C:7](=[O:9])[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:33]=1

Komponenten

8

Edukt 4

HCID 71606Cyclopentylacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Produkt 1

HCID 86714411HCID 86714411, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 16.41 g of cyclopentyl-acetic acid in 600 ml of dry DMF 17.30 g of HOBT, 24.54 g of EDC and 30 ml of DIPEA were added at 0° C. After 1 h 27.51 g of 3-amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester and 30 ml of DIPEA were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by crystallization from diisopropylether to yield 29.35 g (73%) of 3-(2-cyclopentyl-acetylamino)-4-(1-ethyl-propylamino)-benzoic acid methyl ester as an off-white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by crystallization from diisopropylether

Quellen und Nachweise

ORD-Eintrag
ord-1567141a3c60491ca2bdef57e9697e97
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156796B2

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