Hydrochloric Acid → Ammonium Hydroxide

HRID 1388292

Reaktionsgleichung

Reaktionsgleichung von HRID 1388292
[CH2:1]([S:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:16]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([BH3-])#N.[Na+].Cl>C(O)C>[OH-:13].[NH4+:11].[C:17]([C@@H:16]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 193613S-benzyl-L-cysteineHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydride

Produkt 2

HCID 14923Ammonium HydroxideAusbeute 7 %HCID 22825650N-[1(S)-carboethoxy-3-phenylpropyl]-S-benzyl-(R)-cysteine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Stir 10.5 g of S-benzyl-L-cysteine and 11.0 g of 2-oxo-4-phenylbutyric acid, ethyl ester in 1000 ml of absolute ethanol at room temperature for 24 hours. Add 5.28 g of sodium cyanoborohydride and stir the resulting mixture at room temperature for 48 hours. Concentrate this mixture in vacuo at 30° C. to give a white residue. Suspend the residue in ice-water, add concentrated hydrochloric acid to maintain pH 2-4, and stir this mixture for 11/2-2 hours. Absorb this aqueous solution on XAD-2 (Rohm & Haas Co.) resin. Elute the resin with water and then with absolute ethanol. Concentrate the ethanol solution and chromatograph the residue on a column of silica gel using chloroform:isopropanol:7% ammonium hydroxide 1:1:1 (organic layer) to give N-[1(S)-carboethoxy-3-phenylpropyl]-S-benzyl-(R)-cysteine.

Aufarbeitung

  1. concentrationConcentrate this mixture in vacuo at 30° C.
  2. customto give a white residue
  3. temperatureto maintain pH 2-4
  4. stirringstir this mixture for 11/2-2 hours
  5. customAbsorb this aqueous solution on XAD-2 (Rohm & Haas Co.) resin
  6. washElute the resin with water
  7. concentrationConcentrate the ethanol solution and chromatograph the residue on a column of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-76903b21356742eb90462bc9e69eb91e
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04431645

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