Triethylamine → HCID 57968648, Verbindung

HRID 882768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882768
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]3[CH2:18][C@H:17]([O:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:16][NH:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C1COCC1>[CH3:34][S:35]([N:15]1[CH2:16][C@@H:17]([O:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:18][C@H:14]1[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][N:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:6][CH2:7]1)=[O:13])(=[O:37])=[O:36]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44601159HCID 44601159, Verbindung

Produkt 1

HCID 57968648HCID 57968648, VerbindungAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of (2S,4S)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(4-fluoro-phenoxy)-pyrrolidine (29 mg, 0.08 mmol) in THF (0.8 mL) with Et3N (60 μL, 0.4 mmol) was added methanesulfonyl chloride (19 μL, 0.24 mmol). The reaction mixture was allowed to warm to rt and was stirred for 18 h. The mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried and concentrated. Purification by FCC provided the desired product (31 mg, 87%). MS (ESI): mass calcd. for C21H30FN3O4S, 439.19; m/z found, 440.5 [M+H]+. 1H NMR (CDCl3): 7.00-6.94 (m, 2H), 6.83-6.78 (m, 2H), 4.94-4.89 (m, 1H), 4.86 (ddd, J=8.8, 4.4, 4.4 Hz, 1H), 4.10-4.03 (m, 1H), 3.78-3.40 (m, 5H), 3.08 (d, J=4.0 Hz, 3H), 2.84 (dd, J=16.2, 7.8 Hz, 1H), 2.75-2.66 (m, 1H), 2.57-2.26 (m, 4H), 2.25-2.14 (m, 1H), 2.07-1.97 (m, 2H), 1.97-1.71 (m, 4H), 1.69-1.55 (m, 2H).

Aufarbeitung

  1. additionThe mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2 (3×)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customPurification by FCC

Quellen und Nachweise

ORD-Eintrag
ord-1fc13af27cd5413eb34c32334bf3b8e6
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236792B2

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