Ethyl Acetate → 1-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-ethanone
Reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:28])[CH2:15][C:16]1[CH:20]=[CH:19][N:18]([C:21]2[CH:26]=[CH:25][C:24](F)=[CH:23][CH:22]=2)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([C:31]1[CH:36]=[CH:35][C:34](C2C=CC(N3C=CC(CC(O)=O)=C3)=CC=2)=[CH:33][CH:32]=1)#[N:30].C([C@H]1COC(=O)N1)C1C=CC=CC=1.CCOC(C)=O>CCOC(C)=O.CC(OC)(C)C.C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:28])[CH2:15][C:16]1[CH:20]=[CH:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([C:34]3[CH:35]=[CH:36][C:31]([C:29]#[N:30])=[CH:32][CH:33]=3)=[CH:23][CH:22]=2)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
As in Example 14(a) for 1-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-ethanone, 2-[1-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-acetic acid and 4(S)-benzyl-2-oxazolidinone were coupled. Flash column chromatography with 10-25% EtOAc/hex to CH2Cl2 stepwise gradient eluant and subsequent trituration with EtOAc/MTBE/hex provided in 59% yield 1-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-ethanone as a pale yellow amorphous solid. 1H NMR: δ 7.75 (d, 2H, J=8.8 Hz), 7.70 (d, 2H, J=8.5 Hz), 7.65 (d, 2H, J=8.8 Hz), 7.49 (d, 2H, J=8.8 Hz), 7.32-7.25 (m, 3H), 7.17-7.15 (m, 3H), 7.12 (t, 1H, J=2.8 Hz), 6.40 (dd, 1H, J=1.7, 2.8 Hz), 4.74-4.68 (m, 1H), 4.31-4.16 (m, 4H), 3.29 (dd, 1H, J=2.9, 13.6 Hz), 2.80 (dd, H1J=9.4, 13.4 Hz). Anal. Calculated for C29H23N3O3: C, 75.47; H, 5.02; N, 9.11. Found: C, 75.36; H, 5.08; N, 9.15.
Sources & evidence
- ORD record
- ord-983cb96179c14c8f920a5b930fd3a9a6
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174915B1
Reaction notes
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