Hydrochloric Acid → N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine

HRID 1289483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1289483
[OH-].[Na+].C([O:5][C:6](=[O:34])[C@H:7]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=1)[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][N:18]([CH:22]([CH3:24])[CH3:23])[CH2:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])C.Cl.CCOCC>O1CCOCC1>[CH3:24][CH:22]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][C:12]([S:9]([NH:8][C@H:7]([C:6]([OH:34])=[O:5])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=3)(=[O:11])=[O:10])=[CH:13][CH:14]=2)[CH2:19]1)[CH3:23]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 22885593N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine ethyl ester

Produkt 1

HCID 67568068N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanineAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1M Aqueous sodium hydroxide solution (6.0 ml, 6 mmol) was added to a stirred solution of N-[2-(2-propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine ethyl ester (Preparation 25; 1.0 g, 2.19 mmol) in 1,4-dioxan (6.0 ml). After 2.5 hours at room temperature, the reaction mixture was neutralised using 1M hydrochloric acid (6.0 ml) and evaporated to dryness under reduced pressure. The residue was extracted successively with dichloromethane and a mixture of dichloromethane:2-propanol (9:1), then the combined extracts evaporated under reduced pressure to provide a material which, on trituration with ether, gave the title compound as a white powder (780 mg). Rf 0.06 (SS 3). m/e 428 (M+H)+.

Aufarbeitung

  1. customevaporated to dryness under reduced pressure
  2. extractionThe residue was extracted successively with dichloromethane
  3. additiona mixture of dichloromethane:2-propanol (9:1)
  4. customthe combined extracts evaporated under reduced pressure
  5. customto provide a material which

Quellen und Nachweise

ORD-Eintrag
ord-a74a522180714381a1f3d2b82df06609
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750520

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