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Methanesulfonyl chloride → HCID 136358673, Verbindung

HRID 895820
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 895820
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:43]([CH2:44][CH2:45][CH3:46])=[C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[C:26]([S:28]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[CH2:33][CH2:32]4)(=[O:30])=[O:29])[CH:25]=[CH:24][C:23]=3[O:39][CH2:40][CH2:41][CH3:42])[NH:19][C:20](=[O:21])[C:15]2=[N:14]1>N1C=CC=CC=1>[CH2:37]([N:34]1[CH2:35][CH2:36][N:31]([S:28]([C:26]2[CH:25]=[CH:24][C:23]([O:39][CH2:40][CH2:41][CH3:42])=[C:22]([C:18]3[NH:19][C:20](=[O:21])[C:15]4[C:16](=[C:43]([CH2:44][CH2:45][CH3:46])[N:13]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=5[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:14]=4)[N:17]=3)[CH:27]=2)(=[O:30])=[O:29])[CH2:32][CH2:33]1)[CH3:38]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 136481316HCID 136481316, Verbindung

Produkt 1

HCID 136358673HCID 136358673, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methanesulphonyl chloride (0.156 ml, 2.0 mmol) was added to a stirred solution of the title compound of Example 116 (583 mg, 1.0 mmol) in pyridine (8 ml), under nitrogen, and the resulting solution stirred at 50° C. for 18 hours, then evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water, then the separated organic phase washed with brine, dried (MgSO4) and evaporated under reduced pressure. The resulting brown foam was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 99:1 to 98:2 to 97:3), to yield the title compound (32%) as a cream foam. Found: C, 53.96; H, 6.01; N, 14.38. C30H39N7O6S2; 0.60 H2O requires C, 53.89; H, 6.06; N, 14.67%. δ (CDCl3): 0.91 (3H, t), 1.01 (3H, t), 1.19 (3H, t), 1.75 (2H, m), 2.07 (2H, m), 2.40 (2H, q), 2.53 (4H, m), 2.93 (2H, t), 3.07 (3H, s), 3.09 (4H, m), 4.29 (2H, t), 7.16 (2H, m), 7.35 (2H, m), 7.57 (1H, t), 7.82 (2H, d), 8.80 (1H, s), 10.74 (1H, s). LRMS: m/z 658 (M+1)+.

Aufarbeitung

  1. customevaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe separated organic phase washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe resulting brown foam was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ed799ec36be342c4b5150a760d113ea0
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06916927B2

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