Sodium Bicarbonate → HCID 21408245, compound
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@@H:8]([CH2:13][N:14]3[CH2:30][CH2:29][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][NH:19][C:18]4=[O:28])[CH2:16][CH2:15]3)[C@@H:9]2O)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(O)(=O)C.C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]([CH2:13][N:14]3[CH2:30][CH2:29][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][NH:19][C:18]4=[O:28])[CH2:16][CH2:15]3)=[CH:9]2)=[CH:4][CH:3]=1Participants
4
Procedure
trans-8-[(7-Chloro-1,2,3,4-tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4.0 g, see example 190) is added in portions to 25 ml of 20% v/v sulfuric acid/acetic acid and the resulting solution is stirred for 16 hours at room temperature protected from moisture by a drying tube. The acid solution is then warmed for 5 minutes on a steam bath, cooled, poured onto 200 g of ice, and basified with solid sodium bicarbonate. The resulting mixture is extracted with methylene chloride. Concentration of the dried methylene chloride solution provides 2.3 g of a crude solid. Crystallization of this material from absolute ethanol gives 1.6 g of the title compound, melting point 191°-192° C.
Workup
- customprotected from moisture by a drying tube
- temperatureThe acid solution is then warmed for 5 minutes on a steam bath
- temperaturecooled
- extractionThe resulting mixture is extracted with methylene chloride
- customConcentration of the dried methylene chloride solution provides 2.3 g of a crude solid
- customCrystallization of this material from absolute ethanol
Sources & evidence
- ORD record
- ord-e9e3c0ee09464214bfe91f53ebc80e8d
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04051248
Reaction notes
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