Acetic Acid → HCID 54094537, Verbindung

HRID 370840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370840
[CH2:1]1[CH2:20][O:19][C:3]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)([CH2:4][CH2:5][CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:2]1.[C:21]([O:25][C:26](=[O:37])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32](=[O:36])[C@H:33]([CH3:35])[NH2:34])([CH3:24])([CH3:23])[CH3:22].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[C:21]([O:25][C:26](=[O:37])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32](=[O:36])[C@H:33]([CH3:35])[NH:34][CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][CH2:4][C:3]1([O:19][CH2:20][CH2:1][O:2]1)[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)([CH3:23])([CH3:22])[CH3:24]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 12939800tert-Butyl L-alanyl-L-prolinateHCID 20275184HCID 20275184, Verbindung

Produkt 1

HCID 54094537HCID 54094537, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 6,6-ethylenedioxy-2-oxo-6-(2-thienyl)-hexanoate (3 g.) and L-alanyl-L-proline t-butyl ester (2.5 g.) were added to a suspension of freshly activated 4 Å molecular sieve (15 g.) in ethanol (35 ml.) and the mixture was stirred at laboratory temperature for 1 hour. Acetic acid (1.25 ml.) was added, and sodium cyanoborohydride (0.625 g.) was then added in portions during 1 hour. The mixture was stirred at laboratory temperature for 48 hours and then filtered, and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by flash chromatography on a silica gel column using a 40:1 v/v mixture of dichloromethane and methanol as eluant. There was thus obtained as an oil N-[1-ethoxycarbonyl-5,5-ethylenedioxy-5-(2-thienyl)pentyl]-L-alanyl-L-proline t-butyl ester.

Aufarbeitung

  1. stirringThe mixture was stirred at laboratory temperature for 48 hours
  2. filtrationfiltered
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column
  5. additiona 40:1 v/v mixture of dichloromethane and methanol as eluant

Quellen und Nachweise

ORD-Eintrag
ord-fe8a91100ada49b3b8627163c7a67d64
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528282

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