Sodium Hydroxide → HCID 19831143, compound

HRID 5649

Reaction equation

HRID 5649 reaction equation
N1CCCN=[C:2]1[S:7][CH2:8][C:9]1[NH:10][C:11]([CH3:33])=[C:12]([C:29]([O:31][CH3:32])=[O:30])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].Br.BrC[CH2:37][NH2:38].[OH-].[Na+].[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C(OCC)(=O)C.CO.C1C=CC=CC=1>[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45].[NH2:38][CH2:37][CH2:2][S:7][CH2:8][C:9]1[NH:10][C:11]([CH3:33])=[C:12]([C:29]([O:31][CH3:32])=[O:30])[CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 27742172-Bromoethylamine hydrobromideHCID 19796531(-)-2-[(1,4,5,6-Tetrahydropyrimidin-2-yl)thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

Product 1

HCID 19831143HCID 19831143, compound

Reagents, catalysts & solvents 4

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 241BenzeneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (-)-2-[(1,4,5,6-tetrahydropyrimidin-2-yl)thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (g 2), hexadecyltributyl phosphonium bromide (mg 180), 2-bromoethylaminehydrobromide (mg 900), NaOH (35%, ml 8) and benzene is stirred for 40 minutes at room temperature. After the usual work-up, an oily residue is obtained that is dissolved in ethyl acetate and treated with fumaric acid to give 1.9 g of (-)-2-(aminoethylthio)methyl-3-carboethoxy-5-carbomethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine fumarate, m.p. 104°-110° C. [α]D =-11 (C=4 in MeOH).

Workup

  1. customAfter the usual work-up, an oily residue is obtained

Sources & evidence

ORD record
ord-7e2beb4a11a24e89994da680a2a56493
Source dataset
uspto-grants-1993_09
Patent number
US05245039

Linked notes

Loading…