Methanesulfonamide → HCID 49833751, Verbindung

HRID 1614863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614863
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13](O)=[O:14])=[CH:9][CH:8]=2)[CH2:3]1.CCN=C=NCCCN(C)C.Cl.[CH3:30][S:31]([NH2:34])(=[O:33])=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:30][S:31]([NH:34][C:13](=[O:14])[CH2:12][O:11][C:10]1[CH:16]=[CH:17][C:7]([C@@H:4]2[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]2)=[CH:8][CH:9]=1)(=[O:33])=[O:32]

Komponenten

6

Edukt 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 49834134HCID 49834134, Verbindung

Produkt 1

HCID 49833751HCID 49833751, VerbindungAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (2.5 mmol, 585 mg) was dissolved in DCM (30 mL) and cooled to 0° C. on an icebath. EDCI.HCl (3.75 mmol, 720 mg), methanesulfonamide (2.75 mmol, 261 mg) and DMAP (3.75 mmol, 458 mg) was added and the reaction mixture left an additional 15 min on the ice bath. The ice bath was then removed and the reaction was allowed to warm to r.t. over night. Quenched with citric acid (10% aq.) and extracted with DCM, then dried over Na2SO4 and concentrated in vacuo to yield the title compound (745 mg, 95%). 1H NMR (300 MHz, CDCl3) δ 8.84 (bs, 1H), 7.25-7.19 (m, 2H), 6.95-6.85 (m, 3H), 4.58 (s, 2H), 3.58-3.08 (m, 5H), 2.78-2.58 (m, 1H), 2.58-2.15 (m, 5H), 2.15-1.78 (m, 1H).

Aufarbeitung

  1. customThe ice bath was then removed
  2. temperatureto warm to r.t. over night
  3. customQuenched with citric acid (10% aq.)
  4. extractionextracted with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-70d1185ea0d64a428e107a0db793f33a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765676B2

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