Ammonia → HCID 10425391, Verbindung

HRID 243017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243017
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:24]1CCOCC1.C(OC(Cl)=O)C(C)C.N>C1COCC1>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:11]([C:12](=[O:13])[NH2:24])[CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:22])([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine

Produkt 1

HCID 10425391HCID 10425391, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a solution of (S)-4-benzyloxy-2-tert butoxycarbonylamino butyric acid (1.16 g, 3.7 mmol) in anhydrous THF (15 mL) at −15° C. was added N-methylmorpholine (0.41 mL, 3.7 mmol) and isobutylchloroformate (0.51 mL, 3.7 mmol) under a nitrogen atmosphere. After 2 minutes, 33% aqueous ammonia (0.34 mL, 5.6 mmol) was added and the resulting mixture stirred at −15° C. for 2 h. The reaction mixture was left to warm to RT and was partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The combined organic fractions were washed with aqueous 5% NaHCO3, water, dried (MgSO4) and concentrated in vacuo. The resulting white solid was used without further purification (quant. yield). 1H NMR (CDCl3, 300 MHz): δ 7.41-7.25 (5H, m), 6.38 (1H, br s), 5.75 (1H, br s), 5.38 (1H, br s), 4.55-4.45 (2H, m), 4.30 (1H, br s), 3.75-3.52 (2H, m), 2.10-2.00 (2H, m), 1.42 (9H, s).

Aufarbeitung

  1. waitThe reaction mixture was left
  2. temperatureto warm to RT
  3. customwas partitioned between EtOAc
  4. washThe combined organic fractions were washed with aqueous 5% NaHCO3, water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting white solid was used without further purification (quant. yield)

Quellen und Nachweise

ORD-Eintrag
ord-eb61cf843ad6413daf206a522fd227a9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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