Triethylamine → 2-(2-Acetylsulfanyl-acetylamino)-succinic acid 4-tert-butyl ester

HRID 890578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890578
FC1C(O[C:9](=[O:15])[CH2:10][S:11][C:12](=[O:14])[CH3:13])=C(F)C(F)=C(F)C=1F.[NH2:20][C@H:21]([C:30]([OH:32])=[O:31])[CH2:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C>ClCCl>[C:25]([O:24][C:23](=[O:29])[CH2:22][CH:21]([NH:20][C:9](=[O:15])[CH2:10][S:11][C:12](=[O:14])[CH3:13])[C:30]([OH:32])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3569623S-Acetylthioglycolic acid pentafluorophenyl esterHCID 70105704-tert-Butyl hydrogen L-aspartate

Produkt 1

HCID 235971832-(2-Acetylsulfanyl-acetylamino)-succinic acid 4-tert-butyl esterAusbeute 121,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetylsulfanyl-acetic acid pentafluorophenyl ester (1.6 g, 5.3 mmol) and H-Asp(OtBu)-OH (1 g, 5.3 mmol) were mixed in 20 ml of dry dichloromethane (DCM). Then 1.6 ml of triethylamine (11.5 mmol) was added, and the reaction was allowed to proceed at ambient temperature for 3.5 hours. The organic layer was then extracted with 3×15 ml of 1 M sodium carbonate, the combined aqueous fractions were acidified with 100 ml of 1 M sodium hydrogensulfate and extracted with 3×30 ml ethyl acetate. The combined organic fractions were then rinsed with 30 ml of 1 M sodium hydrogensulfate, 30 ml of 5 M NaCl, dried over sodium sulfate, filtered, and evaporated under reduced pressure to yield 1.97 g of 24 as a nearly colorless syrup which was used without further purification. MW=305 (found 306, M+1).

Aufarbeitung

  1. extractionThe organic layer was then extracted with 3×15 ml of 1 M sodium carbonate
  2. extractionextracted with 3×30 ml ethyl acetate
  3. washThe combined organic fractions were then rinsed with 30 ml of 1 M sodium hydrogensulfate, 30 ml of 5 M NaCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e0b4b8f464b34f48a739f70b3d8a0878
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998233B2

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