Acetic Acid → HCID 57893114, Verbindung

HRID 1511454

Reaktionsgleichung

Reaktionsgleichung von HRID 1511454
[CH:1]1([N+:4]#[C-:5])[CH2:3][CH2:2]1.[CH:6]1([CH2:10][C@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[O:13])[CH2:9][CH2:8][CH2:7]1.[C:22](O)(=[O:24])[CH3:23].C(OCC)(=[O:28])C>C(Cl)Cl>[C:22]([O:13][CH:12]([C@@H:11]([NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])[CH2:10][CH:6]1[CH2:9][CH2:8][CH2:7]1)[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:28])(=[O:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2758008IsocyanocyclopropaneHCID 57893126HCID 57893126, Verbindung

Produkt 1

HCID 57893114HCID 57893114, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of cyclopropylisonitrile (1.21 g, 18 mmol), (S)-tert-butyl 1-cyclobutyl-3-oxopropan-2-ylcarbamate (2.95 g, 13 mmol) in methylene chloride(20 mL), was added acetic acid (1.56 g, 26 mmol) at 0° C. After the addition was complete, the reaction mixture was allowed to warm to 25° C. and stirred for another 4 hours. The reaction mixture was diluted with 200 mL ethyl acetate and washed with a saturated solution of sodium bicarbonate, then brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was crystallized from 50 mL of ethyl acetate and hexane (v/v=1/1) to give (3S)-3-(tert-butoxycarbonylamino)-4-cyclobutyl-1-(cyclopropylamino)-1-oxobutan-2-yl acetate (3.8 g) as a white solid.

Aufarbeitung

  1. additionAfter the addition
  2. washwashed with a saturated solution of sodium bicarbonate
  3. dry with materialbrine, and dried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was crystallized from 50 mL of ethyl acetate and hexane (v/v=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-fb0f9205ee744d33ba0aa35a4009f1d5
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211897B2

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