2-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanone → 2-Acetoxy-2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester
Reaction equation
[C:1](OC(C1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)C(N1[C@@H](CC2C=CC=CC=2)COC1(C)C)=O)(=[O:3])[CH3:2].[CH2:39]([O:41][C:42](=[O:62])[CH:43]([C:45]1[O:49][C:48]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:52][CH:51]=2)=[CH:47][CH:46]=1)[OH:44])[CH3:40]>>[CH2:39]([O:41][C:42](=[O:62])[CH:43]([O:44][C:1](=[O:3])[CH3:2])[C:45]1[O:49][C:48]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:52][CH:51]=2)=[CH:47][CH:46]=1)[CH3:40]Participants
Procedure
According to the procedure described in Example 13 for the preparation of 2-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanone, 2-(2-biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester was acylated to furnish in 83% yield 2-acetoxy-2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester which was used without purification. Flash column chromatography with 0-20% EtOAc/hex as eluant gave an analytically pure pink solid, mp 136-140° C. 1H NMR: δ 7.74 (d, 2H, J=8.5 Hz), 7.63 (d, 4H, J=8.5 Hz), 7.46 (t, 2H, =7.4 Hz), 7.36 (t, 1H, J=7.2 Hz), 6.68 (d, 1H, J=3.7 Hz), 658 (d, 1H, J=3.3 Hz), 6.57 (s, 1H), 4.29 (q, 2H, J=7.0 Hz), 2.21 (s, 3H), 1.29 (t, 3H, J=7.2 Hz). Anal. Calculated for C22H20O5 : C, 72.51; H, 5.53. Found: C, 72.61; H, 5.63.
Sources & evidence
- ORD record
- ord-0503d5e26176437ab050d04ce741420b
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008243
Reaction notes
Loading…