HCID 59775598, Verbindung → HCID 69137903, Verbindung

HRID 557466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557466
[C:1]([O:5][C:6](=[O:25])[CH:7]([NH:17][C:18](N1C=CN=C1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH3:26][O:27][C:28](=[O:39])[CH2:29][CH:30]([NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([I:37])[CH:32]=1>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[C@@H:7]([NH:17][C:18]([NH:38][C@H:30]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([I:37])[CH:32]=1)[CH2:29][C:28]([O:27][CH3:26])=[O:39])=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 2

HCID 59775598HCID 59775598, VerbindungHCID 69139351HCID 69139351, Verbindung

Produkt 1

HCID 69137903HCID 69137903, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-[(Imidazole-1-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester (370 mg, 1.05 mmol) was dissolved in DCE (10 mL) and cooled to 0° C. MeoTf (142 μL, 1.25 mmol) was added and the reaction was allowed to proceed for 20 min. (±)-3-Amino-3-(3-iodo-phenyl)-propionic acid methyl ester (356 mg, 1.045 mmol) was added and the reaction was allowed to warm to room temperature and then warmed to 55° C. and stirred overnight. The reaction was diluted with DCM (50 mL) and washed with water (30 mL), 5% aq. Citric acid (30 mL), sat. sodium bicarbonate (30 mL), water (30 mL) and brine (30 mL). The organic layer was dried over sodium sulfate and concentrated to afford the crude product. The product was purified by column chromatography to afford the desired product (303 mg, 0.51 mmol, 49%) as a white foam. 1H NMR (400 MHz, CDCl3) δ 7.66 (s, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.29 (s, 1H), 7.07-7.02 (m, 1H), 5.74 (br, 1H), 5.17 (br, 2H), 4.30 (m, 1H), 3.63 (s, 1.5H), 3.62 (s, 1.5H), 2.88-2.76 (m, 2H), 2.38-2.24 (m, 2H), 2.10-2.00 (m, 1H), 1.90-1.80 (m, 1H), 1.46 (s, 9H), 1.44 (s, 9H).

Aufarbeitung

  1. additionMeoTf (142 μL, 1.25 mmol) was added
  2. temperatureto warm to room temperature
  3. temperaturewarmed to 55° C.
  4. washwashed with water (30 mL), 5% aq. Citric acid (30 mL), sat. sodium bicarbonate (30 mL), water (30 mL) and brine (30 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cd4d2e595feb420ca146d641c69ba256
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058449B2

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