Cesium carbonate → (2R)-2-[N-(4-Allyloxy-3-fluorobenzyl)-N-(4-chlorobenzenesulfonyl)amino]-4-methyl-pentanoic acid amide

HRID 1893848

Reaktionsgleichung

Reaktionsgleichung von HRID 1893848
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[CH:32][C:31]=1[F:38])[CH:27]=[CH2:28]>CN(C=O)C.CCOC(C)=O>[CH2:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][N:11]([C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])[S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])=[CH:32][C:31]=1[F:38])[CH:27]=[CH2:28]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 59001058(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amideHCID 671983671-Allyloxy-4-bromomethyl-2-fluorobenzene

Produkt 1

HCID 10151853(2R)-2-[N-(4-Allyloxy-3-fluorobenzyl)-N-(4-chlorobenzenesulfonyl)amino]-4-methyl-pentanoic acid amideAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2R)-2-(4-chlorobenzenesulfonylamino)-4-methyl-pentanoic acid amide (1.00 g, 3.29 mmol), and Cs2CO3 (1.29 g, 3.95 mmol) in DMF (25 mL) was added 1-allyloxy-4-bromomethyl-2-fluorobenzene (ref.: Graham, S. L. et al., EP Patent Application No. EP 487270 (1992): 0.88 g, 3.67 mmol). The resulting solution was stirred at rt for 18 h. The reaction was then diluted with 9:1 EtOAc:hexanes (350 mL) and washed with H2O (4×200 mL), brine, and dried over Na2SO4, to afford the titled compound (393 mg) as a white solid in 26% yield. MS (ESI), (M+H)+469.1; 1H NMR (CDCl3) δ 7.66 (d, 2H, J=8.1), 7.45 (d, 2H, J=8.1), 7.11 (d, 1H, J=12.0), 6.98 (m, 1H), 6.84 (t, 1H, J=8.0), 6.22 (br s, 1H), 6.04 (m, 2H), 5.42 (m, 1H), 5.16 (br s, 1H), 4.59 (m, 2H), 4.40 (m, 3H), 1.83 (m, 1H), 1.32 (m, 1H), 1.14 (m, 1H), 0.76 (d, 3H, J=7.0), 0.68 (d, 3H, J=7.0).

Aufarbeitung

  1. washhexanes (350 mL) and washed with H2O (4×200 mL), brine
  2. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-c2c1422fc4094ddbb0031b9adfef3847
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513253B2

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