Triethylamine → N-benzyl-N-benzyloxycarbonylmethyl-(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propionamide

HRID 1375040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375040
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[CH2:30]([O:37][C:38](=[O:48])[CH2:39][NH:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[CH2:41]([N:40]([CH2:39][C:38]([O:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:48])[C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 7017908Boc-O-methyl-D-tyrosineHCID 21616628N-benzylglycine benzyl ester hydrochloride

Produkt 1

HCID 54515673N-benzyl-N-benzyloxycarbonylmethyl-(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propionamideAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid (5.14 g) in dichloromethane (50 ml) was added triethylamine (8.49 ml), N-benzylglycine benzyl ester hydrochloride (5.08 g), and 2-chloro-1-methylpyridinium iodide (4.89 g) under ice-bath cooling. After being stirred at room temperature 90 minutes, the reaction mixture was concentrated under reduced pressure, and ethyl acetate (50 ml) and water (50 ml) were added to the residue with stirring, adjusted pH 1 with diluted hydrochloric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (100 g) using a mixed solvent of toluene and ethyl acetate (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give N-benzyl-N-(benzyloxycarbonylmethyl)-(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propionamide (8.57 g) as a syrup.

Aufarbeitung

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and ethyl acetate (50 ml) and water (50 ml)
  3. additionwere added to the residue
  4. stirringwith stirring
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography on silica gel (100 g)
  10. additionThe fractions containing the objective compound
  11. customwere collected
  12. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-62d60a5fe6e44bcb92e658233229ba34
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166598B2

Notizen zur Reaktion

Wird geladen…