Triethylamine → HCID 68408428, Verbindung

HRID 705250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705250
CS([O:5][CH:6]1[CH:11]([CH3:12])[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:8][CH:7]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=O)=O.C(N(CC)CC)C.C[C:38]([O:41]C(OC(OC(C)(C)C)=O)=O)(C)C>N1C=CC=CC=1>[CH3:12][CH:11]1[CH:6]2[CH:7]([N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:38](=[O:41])[O:5]2)[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH2:10]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 722382272-(Tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate

Produkt 1

HCID 68408428HCID 68408428, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (1.0 equiv.) in pyridine (0.2 M) was heated in the microwave at 110° C. for 10 min. The orange reaction was then concentrated under vacuo, the crude was dissolved in ethyl acetate and water, the organic phase was dried with sodium sulfate and concentrated under vacuo. The crude material was dissolved in DCM (0.2 M), triethylamine (1.8 equiv.) was added, followed by Boc2O (1.2 equiv.). The reaction was stirred for 40 min, then concentrated to dryness. The crude material was purified via silica gel column chromatography eluting with hexane and ethyl acetate (1:1) to afford (+/−)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate as a white foam in 66% yield. LC/MS=376.0 (M+H), LC: 3.424 min.

Aufarbeitung

  1. customThe orange reaction
  2. concentrationwas then concentrated under vacuo
  3. dissolutionthe crude was dissolved in ethyl acetate
  4. dry with materialwater, the organic phase was dried with sodium sulfate
  5. concentrationconcentrated under vacuo
  6. dissolutionThe crude material was dissolved in DCM (0.2 M)
  7. concentrationconcentrated to dryness
  8. customThe crude material was purified via silica gel column chromatography
  9. washeluting with hexane and ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-23e5f5969abc4079a276824a37af36b5
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173883B2

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