Phenethylamine → HCID 14444045, Verbindung

HRID 1978284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978284
O=[O+][O-].[CH2:4]([O:11][C:12](=[O:47])[CH2:13][CH:14]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:15](=[O:38])C(C#N)=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:48]([NH2:56])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(Cl)Cl>[NH:39]([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[C@H:14]([C:15]([NH:56][CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:38])[CH2:13][C:12](=[O:47])[O:11][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 1001PhenethylamineHCID 24823OzoneHCID 54318947HCID 54318947, Verbindung

Produkt 1

HCID 14444045HCID 14444045, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Ozone gas was bubbled through a solution of 5 (606 mg, 1 mmol) in CH2Cl2 (20 mL) cooled to −78° C. until its blue color persists within the solution. The excess ozone was purged using argon and phenethylamine (181 mg, 189 μL, 1.5 mmol) was added. The resulting solution was stirred at −78° C. for 1 h and then allowed to warm to r.t. The solvent was removed under reduced pressure and the residue chromatographed on silica gel (0-30% ethyl acetate in hexane) to yield the product as a clear oil which was then recrystallized from ether/hexane (145 mg, 32%): mp 132-134° C.; 1H NMR (CDCl3) δ1.43 (s, 9H, Boc CH3's), 2.81 (t, 2H, NHCH2—CH2—Ph), 3.12 (dd, 1H, 1 of CH2—CO2Bzl), 3.44 (dd, 1H, 1 of CH2—CO2Bzl), 3.55 (t, 2H, NH—CH2—CH2Ph), 5.10 (s, 2H, benzyl CH2), 5.13 (m, 1H, α-CH), 5.51 (d, 1H, urethane NH), 6.92 (br, 1H, amide NH), 7.20 (m, 5H, phenethyl aromatic CH's), 7.30 (m, 5H, benzyl aromatic CH's); FABMS (calculated for C25H31N2O6, 455.2182) m/e 455.2146 (M++1).

Aufarbeitung

  1. customThe excess ozone was purged
  2. additionwas added
  3. temperatureto warm to r.t
  4. customThe solvent was removed under reduced pressure
  5. customthe residue chromatographed on silica gel (0-30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-130deaf46a5d4cc0a753cf0fae546f28
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235929B1

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