Ethyl Acetate → (E)-(7S,10S,13S)-13-tert-Butoxycarbonylamino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diazabicyclo[13.2.2]nonadeca-1(18),4,15(19),16-tetraene-7-carboxylic acid methyl ester

HRID 2371324

Reaktionsgleichung

Reaktionsgleichung von HRID 2371324
[CH3:1][O:2][C:3](=[O:38])[C@@H:4]([NH:8][C:9](=[O:37])[C@@H:10]([NH:14][C:15](=[O:36])[C@@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25]C=C)=[CH:20][CH:19]=1)[CH:11]([CH3:13])[CH3:12])[CH2:5][CH:6]=[CH2:7].CCOC(C)=O>ClC(Cl)CCl>[CH3:1][O:2][C:3]([C@H:4]1[NH:8][C:9](=[O:37])[C@H:10]([CH:11]([CH3:13])[CH3:12])[NH:14][C:15](=[O:36])[C@@H:16]([NH:28][C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[CH2:17][C:18]2=[CH:23][CH:22]=[C:21]([CH:20]=[CH:19]2)[O:24][CH2:25][CH:7]=[CH:6][CH2:5]1)=[O:38]

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 66847339(S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino propionylamino]-3-methylbutyrylamino}-pent-4-enoic acid methyl ester

Produkt 1

HCID 66847119(E)-(7S,10S,13S)-13-tert-Butoxycarbonylamino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diazabicyclo[13.2.2]nonadeca-1(18),4,15(19),16-tetraene-7-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 65741,1,2-TrichloroethaneLösungsmittel

Versuchsvorschrift

Diene 44 (1.80 g, 3.39 mmol) was dissolved in anhydrous 1,1,2-trichloroethane (0.01M) under an atmosphere of argon. GSGC (0.10 equiv) was added. The mixture was heated at reflux for one hour. Two further additions of GSGC (0.10 equiv) were added and after each the reaction mixture was subjected to one h and eighteen h of reflux respectively. This was then cooled and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a brown solid, 0.205 g, 12%. Rf=0.24 (1/1 EtOAc/(50/70) petroleum ether). m.p. 105-107° C.

Aufarbeitung

  1. additionGSGC (0.10 equiv) was added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for one hour
  4. additionTwo further additions of GSGC (0.10 equiv) were added
  5. temperatureof reflux respectively
  6. temperatureThis was then cooled
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  9. customto yield a brown solid, 0.205 g, 12%

Quellen und Nachweise

ORD-Eintrag
ord-0f0e2fb597524808b586a83d932a8bd0
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710178B2

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