L-Methionine → Benzyl (3R)-2-oxo-6-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

HRID 1365981

Reaktionsgleichung

Reaktionsgleichung von HRID 1365981
N[C@H](C(O)=O)CCSC.COC1C=C(OC)C=CC=1C[N:15]1[CH2:21][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][CH2:18][C@@H:17]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:16]1=[O:39]>FC(F)(F)C(O)=O.ClCCl>[O:39]=[C:16]1[C@H:17]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:18][CH:19]=[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:21][NH:15]1

Komponenten

5

Edukt 2

HCID 6137L-MethionineHCID 60037872Benzyl (3R)-1-(2,4-dimethoxybenzyl)-2-oxo-6-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Produkt 1

HCID 60037846Benzyl (3R)-2-oxo-6-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of L-methionine (2.56 g, 17.2 mmol) in trifluoroacetic acid (15 mL) was added to a solution of benzyl (3R)-1-(2,4-dimethoxybenzyl)-2-oxo-6-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (0.84 g, 1.72 mmol) in dichloromethane (20 mL). After 18 h, the mixture was concentrated and water was added. The mixture was extracted with ethyl acetate, washed with water (2×), saturated aqueous sodium bicarbonate (2×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexanes→50% ethyl acetate/hexanes) gave the title compound (0.44 g). MS 337 (M+1).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water (2×), saturated aqueous sodium bicarbonate (2×), saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (5% ethyl acetate/hexanes→50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-508661c5716e41479b225827e20612b6
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893052B2

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