Reaktion #671277

ord-5f2bfc2f7ef040afb7acc22c0f1a776a

Reaktionsgleichung

C[O-].[Na+]
sodium methylate
CC(=O)S[C@H]1C[C@@H](C(=O)N2CC[C@H](NC(=O)CNC(=N)NC(=O)OCc3ccc([N+](=O)[O-])cc3)C2)N(C)C1
(2S,4S)-4-acetylthio-1-methyl-2-[(3S)-3-[2-[3-(4-nitrobenzyloxy-carbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]pyrrolidine
Cl
hydrochloric acid
→
CN1C[C@@H](S)C[C@H]1C(=O)N1CC[C@H](NC(=O)CNC(=N)NC(=O)OCc2ccc([N+](=O)[O-])cc2)C1
(2S,4S)-4-mercapto-1-methyl-2-[(3S)-3[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-yl-carbonyl]pyrrolidine
Ausbeute 58.2%

Edukte

C[O-].[Na+]
sodium methylate
CC(=O)S[C@H]1C[C@@H](C(=O)N2CC[C@H](NC(=O)CNC(=N)NC(=O)OCc3ccc([N+](=O)[O-])cc3)C2)N(C)C1
(2S,4S)-4-acetylthio-1-methyl-2-[(3S)-3-[2-[3-(4-nitrobenzyloxy-carbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]pyrrolidine
Cl
hydrochloric acid

Reagenzien

Keine

Lösungsmittel

CO
methanol
CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated in vacuo
  2. 2
    SonstigeThe resulting residue was chromatographed on a reverse phase column (Cosmosil 75C18PREP (trade mark) manufactured by Nacalai tesque Inc.)
  3. 3
    workup.ADDITIONa mixture of acetonitrile and water as the eluant
  4. 4
    workup.ADDITIONThe fractions containing the desired product
  5. 5
    Einengenconcentrated in vacuo
  6. 6
    workup.ADDITIONThe residue was powdered in a mixture of ethyl acetate and isopropyl ether

Vorschrift

A solution of 28% sodium methylate in methanol (0.5 ml) was added to a solution of (2S,4S)-4-acetylthio-1-methyl-2-[(3S)-3-[2-[3-(4-nitrobenzyloxy-carbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]pyrrolidine (1.5 g) in methanol (30 ml) and stirred at room temperature for 1 hour. At the end of this time, to the resulting mixture was added 1N hydrochloric acid (2.73 ml) and concentrated in vacuo. The resulting residue was chromatographed on a reverse phase column (Cosmosil 75C18PREP (trade mark) manufactured by Nacalai tesque Inc.) using a mixture of acetonitrile and water as the eluant. The fractions containing the desired product were combined and concentrated in vacuo. The residue was powdered in a mixture of ethyl acetate and isopropyl ether. Powdery (2S,4S)-4-mercapto-1-methyl-2-[(3S)-3[2-[3-(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-yl-carbonyl]pyrrolidine (806 mg) was obtained by filtration.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06924279B2uspto-grants-2005_08