(S)-methyl 2-hydroxy-3-phenylpropanoate → (R)-2-[4-(2,3-Dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6-diiodo-phenoxy]-3-phenyl-propionic acid
Reaction equation
[CH3:1][C:2]1[O:26][C:5]2=[CH:6][C:7]3[S:8][C:9]4[C:14]([C:15]=3[C:16]([C:17]3[CH:22]=[C:21]([I:23])[C:20]([OH:24])=[C:19]([I:25])[CH:18]=3)=[C:4]2[C:3]=1[CH3:27])=[CH:13][CH:12]=[CH:11][CH:10]=4.O[C@@H:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32]C)=[O:31]>>[CH3:1][C:2]1[O:26][C:5]2=[CH:6][C:7]3[S:8][C:9]4[C:14]([C:15]=3[C:16]([C:17]3[CH:18]=[C:19]([I:25])[C:20]([O:24][C@H:29]([CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:30]([OH:32])=[O:31])=[C:21]([I:23])[CH:22]=3)=[C:4]2[C:3]=1[CH3:27])=[CH:13][CH:12]=[CH:11][CH:10]=4Participants
3
Procedure
Prepared from 4-(2,3-dimethyl-1-oxa-9-thia-cyclopenta[b]fluoren-4-yl)-2,6 -diiodo-phenol and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester according to the procedure in Example 8 to provide the title compound as a white solid: mp 215-217: NMR (DMSO-d6): δ8.17 (s, 1H), 7.94 (d, J=8 Hz, 1H), 7.85 (d, J=4 Hz, 2H), 7.39-7.30 (m, 5H), 7.22 (dd, J=7 Hz, 1H), 7.16 (dd, J=7, 1 Hz, 1H), 6.87 (d, J=8 Hz, 1H), 5.41 (s, 1H), 3.43 (dd, J=6, 1 Hz, 2H), 2.36 (s, 3H), 1.56 (s, 3H); MS (+FAB): [M+H]+, 745; Anal. Calc. for C31H22I2O4S: C, 50.02; H, 2.98; N, 0.00. Found: C, 47.59; H, 2.98; N, 0.13.
Sources & evidence
- ORD record
- ord-ef79b209610249ad81e6accc0449d118
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06340676B2
Reaction notes
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