Acetonitrile → HCID 178471791, compound

HRID 505284Notes

Reaction equation

HRID 505284 reaction equation
[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

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 57617862(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(bromomethyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-oneHCID 178464370HCID 178464370, compound

Product 1

HCID 178471791HCID 178471791, compound

Procedure

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).

Workup

  1. concentrationconcentrated
  2. customPurification of the residue by PTLC (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a03f8a24037b4fba80a1a76ca9586ae1
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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