HCID 70654349, compound → HCID 70654301, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]1([CH3:24])[C@@H:20]2[C@H:16]([CH2:17][O:18][CH2:19]2)[S:15](=[O:22])(=[O:21])[CH2:14][C:13]([NH2:23])=[N:12]1>C(O)C.[Pd].O1CCCC1>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]2([CH3:24])[C@@H:20]3[C@H:16]([CH2:17][O:18][CH2:19]3)[S:15](=[O:21])(=[O:22])[CH2:14][C:13]([NH2:23])=[N:12]2)[CH:4]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
The crude (3aR,8S,8aS)-rel-8-(2-fluoro-5-nitro-phenyl)-8-methyl-4,4-dioxo-3,3a,4,5,8,8a-hexahydro-1H-2-oxa-4λ6-thia-7-aza-azulen-6-ylamine (73 mg, 204 μmol) was hydrogenated under atmospheric pressure at room temperature in ethanol (5 ml) using palladium on carbon (5%; 39 mg, 18.3 μmol) as the catalyst. After 3 hours the catalyst was filtered and the filtrate evaporated at reduced pressure. In order to complete the reaction, the residue was hydrogenated in a mixture of ethanol (5 ml) and tetrahydrofuran (5 ml) under the aforementioned conditions during 20 hours. Thereafter, the catalyst was filtered, and the filtrate was evaporated at reduced pressure. The crude (3aR,8S,8aS)-rel-8-(5-amino-2-fluoro-phenyl)-8-methyl-4,4-dioxo-3,3a,4,5,8,8a-hexahydro-1H-2-oxa-4λ6-thia-7-aza-azulen-6-ylamine (70 mg) was obtained as brown semisolid material and was engaged in the next step without purification. MS (ISP): m/z=328.3 [M+H]+.
Workup
- filtrationAfter 3 hours the catalyst was filtered
- customthe filtrate evaporated at reduced pressure
- customthe reaction
- filtrationThereafter, the catalyst was filtered
- customthe filtrate was evaporated at reduced pressure
Sources & evidence
- ORD record
- ord-a7fdb0365a724dbba1daac9af86ac962
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067924B2
Reaction notes
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