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

HRID 20117

Reaktionsgleichung

Reaktionsgleichung von HRID 20117
N[C@H](C(O)=O)CCSC.[Br:10][C:11]1[CH2:17][N:16](CC2C=CC(OC)=CC=2OC)[C:15](=[O:29])[C@H:14]([NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:13][CH:12]=1>FC(F)(F)C(O)=O.ClCCl>[Br:10][C:11]1[CH2:17][NH:16][C:15](=[O:29])[C@H:14]([NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:13][CH:12]=1

Komponenten

5

Edukt 2

HCID 6137L-MethionineHCID 60037867Benzyl (3R)-6-bromo-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Produkt 1

HCID 23657091Benzyl (3R)-6-bromo-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamateAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of L-methionine (274 mg, 1.84 mmol) in trifluoroacetic acid (5 mL) was added to a solution of benzyl (3R)-6-bromo-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (90 mg, 0.184 mmol) in dichloromethane (5 mL). After 18 h, the mixture was concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (17 mg). MS 339 (M+1).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-9f6e6e77a9204b188026d604d11c70f4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745427B2

Verknüpfte Notizen

Wird geladen…