Acetonitrile → HCID 178471791、化合物

反応式

[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH2:30]Br)[C@H:14]2[CH3:32])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(NC[C@H:39]1[CH2:44][CH2:43][C@H:42]([C:45]([O:47][CH2:48][CH3:49])=[O:46])CC1)C.CC[N:52]([CH:56]([CH3:58])C)[CH:53]([CH3:55])C.[CH3:59][C:60]#N>>[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[CH2:30][N:52]([CH2:53][C@H:55]3[CH2:39][CH2:44][C@H:43]([CH2:42][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:60][CH2:59]3)[CH2:56][CH3:58])[C@H:14]2[CH3:32])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

参加物

反応物 4

HCID 6342Acetonitrile

HCID 81531Diisopropylethylamine

HCID 57617862(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

HCID 178464370HCID 178464370、化合物

生成物 1

HCID 178471791HCID 178471791、化合物

実験手順

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (50.4 mg, 0.0894 mmol) in MeCN (1 mL) was added ethyl trans-4-[(ethylamino)methyl]cyclohexanecarboxylate (20 mg, 0.0894 mmol) and i—Pr2NEt (240 μL, 0.179 mmol). The reaction was stirred at room temperature for 16 hours and then concentrated. Purification of the residue by PTLC (50% EtOAc/hexanes) afforded ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)benzyl](ethyl)amino]methyl}cyclohexyl)acetate. Rf=0.42 (50% EtOAc/hexanes). LCMS=711.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89 (s, 1H), 7.79 (s, 2H), 7.56-7.52 (m, 2H), 7.48 (s, 1H), 5.73 (d, J=7.8 Hz, 1H), 5.00 (d, J=16.0 Hz, 1H), 4.46 (d, J=16.2 Hz, 1H), 4.11 (q, J=6.9 Hz, 2H), 4.04-3.98 (m, 1H), 3.66-3.53 (m, 2H), 2.47 (q, J=7.1 Hz, 2H), 2.19 (d, J=7.1 Hz, 2H), 2.14 (d, J=7.1 Hz, 2H), 1.80-1.64 (m, 5H), 1.38-1.32 (m, 1H), 1.23 (t, J=7.1 Hz, 3H), 0.99 (t, J=7.1 Hz, 3H), 0.97-0.79 (m, 4H), 0.76 (d, J=6.6 Hz, 3H).