Sodium → N-[4-({[tert-butyl(dimethyl)-silyl]oxy}methyl)-2-fluorophenyl]acrylamide
Reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])=[C:10]([F:19])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH:22][C:23]([C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)[C:24]([O:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([NH:33][CH3:34])[CH2:29][CH2:28]1)=[O:25].[Na]>>[OH:22][C:23]([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)([C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)[C:24]([O:26][C@H:27]1[CH2:28][CH2:29][C@H:30]([N:33]([CH2:17][CH2:16][C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:21])[CH3:20])=[CH:9][C:10]=2[F:19])=[O:18])[CH3:34])[CH2:31][CH2:32]1)=[O:25].[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])=[C:10]([F:19])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH:22][C:23]([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)([C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)[C:24]([O:26][C@H:27]1[CH2:28][CH2:29][C@H:30]([NH:33][CH3:34])[CH2:31][CH2:32]1)=[O:25]Participants
6
Reactant 3
Product 3
Procedure
The title compound was obtained (44%) from N-[4-({[tert-butyl(dimethyl)-silyl]oxy}methyl)-2-fluorophenyl]acrylamide (intermediate 117; 0.5 g, 1.62 mmol), trans-4-(methylamino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 5, 0.51 g, 1.46 mmol) and sodium triacetoxyhydroborate (1.1 g, 5.24 mmol) following the experimental procedure as described in intermediate 30, followed by a purification by preparative reversed-phase HPLC (System 2).
Sources & evidence
- ORD record
- ord-08294f6ab4a54211bf7c6d94c1771d7a
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315463B2
Reaction notes
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