Ammonia → Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

HRID 2047296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047296
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=[N:27]C=2C=1.CCN=C=NCCCN(C)C.Cl.N>C(O)(C)C>[C:1]([O:5][C:6](=[O:7])[CH2:8][CH2:9][C:10]1[C:18]([CH3:19])=[CH:17][C:13]([C:14](=[O:15])[NH2:27])=[CH:12][C:11]=1[CH3:20])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 594979324-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid

Produkt 1

HCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoateAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

To a suspension of 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid (8.00 g, 28.7 mmol) in isopropanol (100 mL), HOBt (4.27 g, 31.6 mmol) followed by EDC hydrochloride (6.34 g, 33.1 mmol) is added. After stirring at rt for 1 h, 25% aq. ammonia (16.1 mL) is added. Stirring is continued for 30 min before the isopropanol is evaporated under reduced pressure. The remaining solution is diluted with isopropyl acetate (200 mL), washed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL) followed by water (50 mL), dried over MgSO4, filtered, concentrated and dried to give 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.5 g) as an off-white solid.

Aufarbeitung

  1. additionis added
  2. stirringStirring
  3. customis evaporated under reduced pressure
  4. additionThe remaining solution is diluted with isopropyl acetate (200 mL)
  5. washwashed three times with approximately 0.5 N aq. NaHCO3 solution (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cf4c66fe557b4196b1ce716f1d5fcfb4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592460B2

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