Heptane → (2R)-2-Fluoro-2-methyl-N-[(S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N'-(3,3,4,4,4-pentafluoro-butyl)-malonamide
Reaction equation
[F:1][C:2]([CH3:35])([C:23]([NH:25][CH2:26][CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])=[O:24])[C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[N:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:4].CCCCCCC>C(O)(C)C>[F:1][C@:2]([CH3:35])([C:23]([NH:25][CH2:26][CH2:27][C:28]([F:33])([F:34])[C:29]([F:32])([F:31])[F:30])=[O:24])[C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[N:11]([CH3:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2)=[O:4]Participants
Procedure
The separation of 0.2 g of the two isomers of (2RS)-2-fluoro-2-methyl-N-[(S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N′-(3,3,4,4,4-pentafluoro-butyl)-malonamide (Example WG) was performed on a preparative chiral HPLC column (CHIRALPAK® AD, pressure: flow: 35 ml/min) using a 4:1 mixture of n-heptane and isopropanol as the eluent. There were obtained 23 mg [11% of theory, optical integrity >99.5% d.e., MS: m/e=502 (M+H)+] of the first eluting isomer (2R)-2-Fluoro-2-methyl-N-[(S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N′-(3,3,4,4,4-pentafluoro-butyl)-malonamide and 22 mg [11% of theory, optical integrity >99.5% d.e., MS: m/e=502 (M+H)+] of the later eluting isomer (2S)-2-fluoro-2-methyl-N-[(S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N′-(3,3,4,4,4-pentafluoro-butyl)-malonamide, each as a yellowish foam.
Sources & evidence
- ORD record
- ord-8acd9bb74780491d89d2e6e9caf32907
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07160875B2
Reaction notes
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