1,2-Dibromoethane → 2-[3-Cyclopropylmethyl-4-(2-nitro-benzene-sulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

HRID 720166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720166
[CH3:1][O:2][C:3](=[O:37])[CH:4]([NH:16][C:17](=[O:36])[CH:18]([NH:23][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])(=[O:26])=[O:25])[CH2:19][CH:20]1[CH2:22][CH2:21]1)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.Br[CH2:39][CH2:40]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:37])[CH:4]([N:16]1[CH2:40][CH2:39][N:23]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])(=[O:25])=[O:26])[CH:18]([CH2:19][CH:20]2[CH2:21][CH2:22]2)[C:17]1=[O:36])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 695877582-[3-Cyclopropyl-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester

Produkt 1

HCID 695880642-[3-Cyclopropylmethyl-4-(2-nitro-benzene-sulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 2-[3-cyclopropyl-2-(2-nitro-benzenesulfonylamino)-propionylamino]-3-naphthalen-2-yl-propionic acid methyl ester, 12, (3.46 g, 6.59 mmol) and 1,2-dibromoethane (12.38 g, 65.9 mmol) in DMF (40 mL) is added potassium carbonate (9.10 g, 65.8 mmol). The reaction mixture is stirred for 15 hours at 65° C., cooled and quenched with aqueous NH4Cl solution. The mixture is then extracted several times with EtOAc and the combined extracts dried over Na2SO4 and concentrated in vacuo. The resulting residue is purified over silica gel (hexanes/EtOAc, 1:2) to afford 3.57 g (98% yield) of the desired product. 1H NMR (300 MHz, CD3OD) δ 8.01–8.08 (m, 1H), 7.58–7.84 (m, 7H), 7.43–7.52 (m, 2H), 7.35 (dd, J=8.4 Hz, 1H), 5.38 (dd, J=11.7, 4.8 Hz, 1H), 4.33–4.44 (m, 1H), 3.76–3.88 (m, 1H), 3.69 (s, 3H), 3.21–3.66 (m, 4H), 2.99–3.14 (m, 1H), 1.40–1.53 (m, 1H), 1.02–1.16 (m, 1H), −0.14–−0.02 (m, 3H), −0.34–−0.20 (m, 2H); MS (ESMS) m/z 552.2 (M+H)+.

Aufarbeitung

  1. temperaturecooled
  2. customquenched with aqueous NH4Cl solution
  3. extractionThe mixture is then extracted several times with EtOAc
  4. dry with materialthe combined extracts dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified over silica gel (hexanes/EtOAc, 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-382ee30e434a403d8ab0419b23c3701e
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132539B2

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