Sodium Bicarbonate → (3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamide

HRID 342911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342911
[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][N:14]2[C@H:23]([C:24]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][C@H:21]3[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:15]2)[O:11]C(=O)[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC(S([O-])(=O)=O)=CC=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:9][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:12]([OH:11])[CH2:13][N:14]1[C@H:23]([C:24]([NH:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:22][C@H:21]2[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15]1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 86753580(3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-yl methyl]-N-tert.-butyl-decahydro-isoquinoline-3-carboxamide p-nitrobenzenesulphonate

Produkt 1

HCID 9865804(3S,4aS,8aS)-2-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-tert-butyldecahydroisoquinoline-3-carboxamideAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

34.7 g of (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-yl methyl]-N-tert.-butyl-decahydro-isoquinoline-3-carboxamide-p-nitrobenzenesulphonate were divided between 110 ml of ethyl acetate and 110 ml of saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate and the ethyl acetate extracts washed with 110 ml of saturated sodium bicarbonate and with water. The organic extracts were evaporated and the residue diluted with 55 ml of ethanol and combined with stirring with a solution of 11.0 g of sodium hydroxide in 55 ml of water. The mixture was refluxed for 5 hours, diluted with 55 ml of water and cooled to room temperature. The suspension was filtered and the residue washed with water until the filtrate was neutral. The residue was evaporated and yielded 20.7 g (93%) 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.-butyl-decahydro-(4aS, 8aS)-isoquinoline-3(S)-carboxamide, melting point 175°-176°.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe ethyl acetate extracts washed with 110 ml of saturated sodium bicarbonate and with water
  3. customThe organic extracts were evaporated
  4. additionthe residue diluted with 55 ml of ethanol
  5. temperatureThe mixture was refluxed for 5 hours
  6. additiondiluted with 55 ml of water
  7. filtrationThe suspension was filtered
  8. washthe residue washed with water until the filtrate
  9. customThe residue was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f3f843822a61450eac651ce621cc58c0
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859248

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