Hydrazine hydrate (1:1) → (2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine

HRID 1034488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034488
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(=O)C)[CH2:14][C@H:13]2[CH2:21][N:22]2C(=O)C3=CC=CC=C3C2=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.NN>ClCCl.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([SH:17])[CH2:14][C@H:13]2[CH2:21][NH2:22])=[O:11])=[CH:33][CH:34]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 57106506(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine

Produkt 1

HCID 57083137(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-aminomethyl-4-mercaptopyrrolidineAusbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine (4.92 g: 10.18 mmole) in a mixture of dichloromethane (15 ml) and methanol (75 ml), hydrazine hydrate (1.53 ml: 3 eq.) is added. The mixture is warmed to removed dichloromethane and heated to reflux for 1 hour and 10 minutes. The reaction mixture is concentrated in vacuo. The residue is diluted with dichloromethane and filtered. The filtrate is washed with water, dried over magnesium sulfate, and concentrated in vacuo to give crude (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-aminomethyl-4-mercaptopyrrolidine (3.3 g). Yield: Quantitative. NMR δ(CDCl3) ppm: 1.63 to 1.90(m, 1H), 2.48 to 2.68(m, 1H), 2.86 to 3.43(m, 4H), 3.65 to 4.23(m, 2H), 5.22(s, 2H), 7.52(d, J=9 Hz, 2H), 8.23 (d, J=9 Hz, 2H).

Aufarbeitung

  1. additionis added
  2. temperatureThe mixture is warmed
  3. customto removed dichloromethane
  4. temperatureheated
  5. temperatureto reflux for 1 hour and 10 minutes
  6. concentrationThe reaction mixture is concentrated in vacuo
  7. additionThe residue is diluted with dichloromethane
  8. filtrationfiltered
  9. washThe filtrate is washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8de40d7504ec4ca2bec481923ec6aa75
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05317016

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