Sodium Hydroxide → HCID 14580329, compound

HRID 1905396Notes

Reaction equation

[OH:1][C@H:2]([CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH:19]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([CH3:29])[NH:22][C:21]([CH3:30])=[C:20]1[C:31]([O:33][CH3:34])=[O:32].[OH-].[Na+]>[N+]([O-])(O)=O>[OH:1][C@H:2]([CH2:35][O:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[C:19]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([CH3:29])[N:22]=[C:21]([CH3:30])[C:20]=1[C:31]([O:33][CH3:34])=[O:32]

Participants

Conditions

Temperature: 80 °C

Procedure

In 100 ml of 2N nitric acid under vigorously stirring was suspended 10 g of dimethyl 4-[2-[4-[[(S)-2-hydroxy-3phenoxypropyl]amino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and the suspension heated at 80° C. for one hour. After cooling, the reaction mixture was made alkaline with a 10% sodium hydroxide aqueous solution and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent distilled off under reduced pressure. The resultant residue was subjected to silica gel column chromatography and eluted with chloroform - methanol (98:2) to give 4.8 g of oily dimethyl 4-[2-[4-[[(S)-2-hydroxy-3-phenoxypropyl]amino] butoxy]-5-nitrophenyl]-2,6-dimethylpyridine-3,5-dicarboxylate

Workup

temperatureAfter cooling
extractionextracted with chloroform
dry with materialThe extract was dried over anhydrous magnesium sulfate
distillationthe solvent distilled off under reduced pressure
washeluted with chloroform - methanol (98:2)

Sources & evidence

ORD record: ord-b025c0ceea824f0c88b1d2e6a38154a5
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04843085

Reaction notes

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