Chloroacetyl chloride → (2S,4S)-2-(chloroacetylamino)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1650846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650846
[NH2:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([S:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][N:4]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:29].[Cl:41][CH2:42][C:43](Cl)=[O:44].C(N(CC)CC)C>O1CCCC1.O>[Cl:41][CH2:42][C:43]([NH:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([S:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:5][N:4]1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:29])=[O:44]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 15056148(2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

Produkt 1

HCID 57097948(2S,4S)-2-(chloroacetylamino)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (7.78 g) in a mixture of tetrahydrofuran (120 ml) and water (40 ml) was added dropwise chloroacetyl chloride (1.23 ml) with stirring under ice-cooling, keeping the pH 8-10 with triethylamine. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was evaporated in vacuo to remove the organic layer. The resulting residue was extracted twice with ethyl acetate (100 ml). The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give (2S,4S)-2-(chloroacetylamino)methyl-1-(4-nitrobenzyloxy-carbonyl)-4-(triphenylmethylthio)pyrrolidine (7.35 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. customThe reaction mixture was evaporated in vacuo
  4. customto remove the organic layer
  5. extractionThe resulting residue was extracted twice with ethyl acetate (100 ml)
  6. washThe extract was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ce13f16cb83492fb07b37b5ca48601f
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925838

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