Triethylamine → (4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-one

HRID 1246376

Reaktionsgleichung

Reaktionsgleichung von HRID 1246376
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[NH2:9][C@@H:10]([CH:25]([CH3:27])[CH3:26])[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[CH:25]([C@H:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][C:2](=[O:3])[NH:9]1)([CH3:27])[CH3:26]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 854145(S)-(-)-2-Amino-3-methyl-1,1-diphenyl-1-butanol

Produkt 1

HCID 9838646(4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-oneAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Trichloromethyl chloroformate (2.71 g, 13.7 mmol) was added to a mixture of (S)-2-amino-3-methyl-1,1-diphenyl-1-butanol (2) (3.18 g, 12.45 mmol) and triethylamine (2.68 g, 26.52 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 2 h at the same temperature and then poured into a brine solution (250 ml). The aqueous layer was made basic with NaOH pellets and organic products were extracted into AcOEt (5×200 ml). Combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. The resulting crude product was washed with diethyl ether to obtain the title compound (3) (3.03 g, 86%) as a white solid. m.p. 250–251° C. (liti 250–251° C.). [α]D25=−201.59° (c, 0.0252 in DMSO). δH (DMSO-d6) 0.51 (3H, d, 3J=6.60 Hz, CH3), 0.92 (3H, d, 3J=7.20 Hz, CH3), 1.86 (1H, ds, 3J=2.10 and 6.60 Hz, CH—Me2), 4.46 (1H, d, 3J=6.5 Hz, CH—NH2), 7.24–7.72 (10H, m, Ar—H), 8.14 (1H, s, NH). δC 15.2 and 20.9 (CH3), 29.8 (CH), 64.9 (CH—NHCO), 88.4 (C—O), 125.8, 126.2, 127.9, 128.4, 128.8 and 129.1 (Ar), 140.5 and 146.1 (α-Ar), 158.1 (C═O). Ir 3295 (NH2), 1765 and 1745 (C═O). m/e (CI—NH3) 282 (MH+, 25%), 299 (MNH4+, 8%), 238 (96%), 223 (100%), 72 (100%).

Aufarbeitung

  1. extractionwere extracted into AcOEt (5×200 ml)
  2. dry with materialCombined organic extracts were dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting crude product was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-56149978dbb04527ba3483bc9c2c6d19
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07126028B1

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