Sodium Chloride → N,N'-di-(3,4-dimethoxyphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

HRID 2269829

Reaktionsgleichung

Reaktionsgleichung von HRID 2269829
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][S:8][C@@H:9]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([NH:12][CH:13]([C:17]([OH:19])=O)[C:14](O)=[O:15])=[O:11])=[CH:5][CH:4]=1.[Cl-].[Na+].CN1[CH2:37][CH2:36][O:35][CH2:34]C1.Cl.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH2:49][CH2:50][NH2:51])[CH:44]=[CH:45][C:46]=1[O:47][CH3:48].Cl.C(N=C=N[CH2:58][CH2:59][CH2:60][N:61](C)C)C.O.ON1C2C=CC=CC=2N=N1.[O:75]1[CH2:79][CH2:78][CH2:77][CH2:76]1>ClCCl.C(OCC)(=O)C.ClCCl>[CH3:34][O:35][C:36]1[CH:37]=[C:58]([CH:78]=[CH:77][C:76]=1[O:75][CH3:79])[CH2:59][CH2:60][NH:61][C:17](=[O:19])[CH:13]([NH:12][C:10](=[O:11])[C@@H:9]([S:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]([NH:51][CH2:50][CH2:49][C:43]1[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:41]([O:40][CH3:39])[CH:42]=1)=[O:15]

Komponenten

10

Edukt 7

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 71555Homoveratrylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 540116352-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonic acid

Produkt 1

HCID 20713096N,N'-di-(3,4-dimethoxyphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel2×

Versuchsvorschrift

Combine 2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonic acid (prepared by the method of Preparation 5, 0.476 g, 63% acid/37% sodium chloride, 0.74 mmol), and N-methylmorpholine (0.27 mL, 2.4 mmol), 3,4-dimethoxyphenylethylamine hydrochloride (0.50 g, 2.3 mmol), dichloromethane (9 mL), and tetrahydrofuran (1 mL). Cool in an ice bath. Add, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloric acid salt (0.314 g, 1.64 mmol) and 1-hydroxybenztriazole hydrate (0.22 g, 1.64 mmol). After 1 day, concentrate in vacuo and partition the concentrated reaction mixture between an aqueous 5% sulfuric acid solution and ethyl acetate. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 2/1 dichloromethane/ethyl acetate and then 1/1 dichloromethane/ethyl acetate to give the title compound.

Aufarbeitung

  1. temperatureCool in an ice bath
  2. additionAdd
  3. concentrationconcentrate in vacuo
  4. custompartition
  5. customthe concentrated reaction mixture between an aqueous 5% sulfuric acid solution and ethyl acetate
  6. customSeparate the layers
  7. extractionextract the organic layer with a saturated aqueous sodium bicarbonate solution
  8. dry with materialDry the organic layer over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-92afdf324be04aa7b833712f5c68d2b5
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329550B1

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