Phosphoric acid, bis(1,1-dimethylethyl) 2-hydroxyethyl ester → (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-(di-tert-butoxy-phosphoryloxy)-ethyl ester
Reaction equation
[C:1]([O:5][P:6]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])([O:8][CH:9](C)[CH2:10][O:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=2)[C@@:16]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])([F:27])[C:15]1=[O:37])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].OCCOP(=O)(OC(C)(C)C)OC(C)(C)C>>[C:40]([O:39][P:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][CH2:9][CH2:10][O:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([F:26])([F:24])[F:25])[CH:21]=2)[C@@:16]([C:28]2[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:29]=2[O:35][CH3:36])([F:27])[C:15]1=[O:37])=[O:13])=[O:7])([CH3:43])([CH3:42])[CH3:41]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared analogously to (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid 2-(di-tert-butoxy-phosphoryloxy)-propyl ester ((S)-VII, n=2) in 52% yield, using phosphoric acid di-tert-butyl ester 2-hydroxy-ethyl ester. 1H NMR (CDCl3, 500 MHz) δ 8.29 (s, 1H), 7.77 (d, 1H), 7.43 (d, 1H), 7.35 (d, 1H), 7.27 (d, 1H), 6.75 (d, 1H), 4.67 (m, 2H), 4.31 (m, 2H), 3.53 (s, 3H), 1.47 (s, 18H); LC-MS, 640.15 (MH+, 96); 31P NMR (CDCl3, 500 MHz) δ−8.71; 19F NMR (CDCl3, 500 MHz) δ−63.3, 153.6.
Sources & evidence
- ORD record
- ord-01184a3e908046f8ae72bffa7fce3268
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06930100B2
Reaction notes
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