Sodium Bicarbonate → HCID 67932559, compound

HRID 1461402Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

0.3 ml of 5% NaHCO3 aqueous solution are added to a solution of the most polar diastereoisomer of 2-[3-formyloxy-3-phenyl-propyl]-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (2.5 g) in methanol (20 ml). The mixture is refluxed for 30 minutes, then it is cooled to 25° C. and evaporated to a small volume (2 ml) under reduced pressure. The sticky mass is diluted with ethyl ether (70 ml) and water (30 ml) and the phases are separed. The organic phase is washed with water (2×30 ml) and dried on sodium sulphate. The solvent is evaporated under reduced pressure, obtaining 2.3 g of the most polar diastereoisomer of 2-(3-phenyl-3-hydroxy-propyl)-3-carbomethoxy-5-carboethoxy-6-methyl-4-(m-nitrophenyl)-1,4-dihydropyridine as yellow foam.

Workup

temperatureThe mixture is refluxed for 30 minutes
customevaporated to a small volume (2 ml) under reduced pressure
additionThe sticky mass is diluted with ethyl ether (70 ml) and water (30 ml)
washThe organic phase is washed with water (2×30 ml)
customdried on sodium sulphate
customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record: ord-f6c740fe954f470ebbe1647addc3dba3
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075324

Reaction notes

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