Triethylamine → (S)-4-(4-Fluorobenzyl)oxazolidine-2,5-dione

HRID 751673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751673
C([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C(OCC)(=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@H:9]2[C:10](=[O:12])[O:11][C:6](=[O:5])[NH:8]2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Produkt 1

HCID 59753664(S)-4-(4-Fluorobenzyl)oxazolidine-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2(S)-tert-butoxycarbonylamino-3-(4-fluorophenyl)propionic acid (1.5 g, 5.29 mmol) in ethyl acetate (100 mL) under an argon atmosphere was added triphosgene (628 mg, 2.12 mmol). To the solution was added triethylamine (0.8 mL 5.76 mmol,) over 1 min, and the reaction stirred for 72 h at rt. The reaction mixture was filtered, and the filtrate concentrated in vacuo to yield an oily residue. The crude material was crystallised from cold dichloromethane and petroleum ether to give the title compound. δH (CD3OD): 7.20 (2H, m), 7.10 (2H, m), 5.86 (1H, s, (NH)), 4.58 (1H, s), 3.33–3.23 (2H, m), 3.11–3.00 (1H, m).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto yield an oily residue
  4. customThe crude material was crystallised from cold dichloromethane and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-b5521b9e8fce4ff29543c84c4e48f37b
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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