Sodium → Etalocib
Reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([OH:28])[C:25]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[CH:24][C:23]=2[CH2:36][CH3:37])[C:12]=1[CH2:38][CH2:39][CH3:40].[Na]>>[CH2:38]([C:12]1[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([OH:28])[C:25]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[CH:24][C:23]=2[CH2:36][CH3:37])=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:41])=[O:2])[CH2:39][CH3:40]Participants
Procedure
2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid methyl ester (21.5 g, 38.5 mmoles) was hydrolyzed as described above for the preparation of Example 7. The acid was converted to the sodium salt and purified as described in Example 7 to provide 16.7 g (77%) of the desired title product as a white amorphous solid: NMR (DMSO-d6) 10.50 (bs, 1H, --OH), 7.51 (m, 3H), 7.20 (t, J=7.4 Hz, 1H), 7.13 (m, 2H), 7.00 (m, 2H), 6.95 (s, 1H), 6.67 (dd, J=8.2, 3.3 Hz, 2H), 6.62 (s, 1H), 6.26 (d, J=8.2 Hz, 1H), 4.14 (t, J=5.8 Hz, 2H), 4.02 (t, J=5.7 Hz, 2H), 2.60 (t, J=6.8 Hz, 2H), 2.47 (q, J=7.3 Hz, 2H), 2.16 (t, J=5.9 Hz, 2H), 1.45 (hextet, J=7.5 Hz, 2H), 1.07 (t, J=7.5 Hz, 3H), 0.81 (t, J=7.4 Hz, 3H); MS-FAB m/e 568 (38, p+1), 567 (100, p), 544 (86), 527 (77), 295 (65), 253 (45); IR (KBr, cm-1) 3407 (b), 2962, 1603, 1502, 1446, 1395, 1239, 1112. Analysis for C33H32O6FNa: Calc: C, 69.95; H, 5.69; F, 3.35; Found: C, 69.97; H, 5.99; F, 3.52.
Workup
- customas described above for the preparation of Example 7
- custompurified
Sources & evidence
- ORD record
- ord-52c32f9250244988a132ec4c27b8f8cf
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05478857
Reaction notes
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