Pyridine → (4-Nitrophenyl)methyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-mercapto-1-pyrrolidinecarboxylate

HRID 1034483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034483
[N+:1]([C:4]1[CH:44]=[CH:43][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:14][C@H:13]2[CH2:37][NH:38][S:39](=[O:42])(=[O:41])[NH2:40])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1>O1CCCC1.O.ClCCl.CO.S.[N+]([O-])([O-])=O.[Ag+]>[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[CH2:37][NH:38][S:39](=[O:41])(=[O:42])[NH2:40])=[O:11])=[CH:43][CH:44]=1)([O-:3])=[O:2]

Komponenten

9

Edukt 2

HCID 1049PyridineHCID 57161027(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine

Produkt 1

HCID 10200398(4-Nitrophenyl)methyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-mercapto-1-pyrrolidinecarboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 24470Silver NitrateKatalysatorHCID 402Hydrogen SulfideLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-tritylthiopyrrolidine (668 mg: 0.95 mmole) in tetrahydrofuran (6 ml), a solution of pyridine (0.254 ml: 2.7 eq.) and silver nitrate (403 mg: 2.5 eq.) in water (2 ml) is added under ice cooling. The mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with dichloromethane (3 ml) and methanol (3 ml), and hydrogen sulfide is bubbled through it under ice cooling for 10 minutes. The resulting precipitate is removed by filtering. The filtrate is diluted with dichloromethane, washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate) to give (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-sulfamoylaminomethyl-4-mercaptopyrrolidine (233 mg). Yield: 63%. NMR δ(CDCl3 -CD3OD) ppm: 1.42(t, J=7 Hz, 1H), 1.65 to 1.93(m, 1H), 2.48 to 2.70 (m, 1H), 3.05 to 3.63(m, 4H), 3.93 to 4.16(m, 2H), 5.22(s, 2H), 7.53(d, J=8 Hz, 2H), 8.23(d, J=8 Hz, 2H). IR ν (CHCl3) cm-1 : 3276br, 1692, 1607.

Aufarbeitung

  1. customis bubbled through it under ice cooling for 10 minutes
  2. customThe resulting precipitate is removed
  3. filtrationby filtering
  4. additionThe filtrate is diluted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0207ada31fd342cf86e23cafffcbd290
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05317016

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