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4-Chlorobenzenesulfonyl chloride → HCID 69920461, Verbindung

HRID 1250862
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1250862
[NH2:1][C@H:2]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:20]([O:19][C:17]([C@@H:2]([NH:1][S:31]([C:28]1[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=1)(=[O:33])=[O:32])[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 699227854-[4-((2S)-2-amino-2-tert-butoxycarbonyl-ethyl)-phenoxy]-butyric acid

Produkt 1

HCID 69920461HCID 69920461, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

200 mg of 4-[4-((2S)-2-amino-2-tert-butoxycarbonyl-ethyl)-phenoxy]-butyric acid were dissolved in 2 ml of DMF and cooled to 0° C. 220 mg of 4-chlorobenzenesulfonyl chloride and 270 mg of diisopropylethylamine were added and the reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was cooled to −25° C. for 16 hours and then warmed to room temperature. The reaction was quenched by the addition of water, and the mixture was extracted three times with dichloromethane. The combined organic phases were dried with sodium sulfate, filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with dichloromethane/methanol/water/acetic acid (9/1/0.1/0.1). Yield 84 mg. MS (ES+): m/e=498.1 (M+H)+; 442.1.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to −25° C. for 16 hours
  2. temperaturewarmed to room temperature
  3. customThe reaction was quenched by the addition of water
  4. extractionthe mixture was extracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol/water/acetic acid (9/1/0.1/0.1)

Quellen und Nachweise

ORD-Eintrag
ord-50f4375e25f64d2e8bea1670f24dbc54
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06340679B1

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