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Hydrochloric Acid → ZD 7114 hydrochloride

HRID 1651126
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1651126
[OH:1][CH:2]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][C:14]([O:16]C)=O)=[CH:10][CH:9]=1.[CH3:28][O:29][CH2:30][CH2:31][NH2:32].CCOCC.[ClH:38]>ClCCl>[ClH:38].[OH:1][C@H:2]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([NH:32][CH2:31][CH2:30][O:29][CH3:28])=[O:16])=[CH:18][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 80182-MethoxyethylamineHCID 132305HCID 132305, Verbindung

Produkt 1

HCID 9890216ZD 7114 hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(-)-Methyl 4-[2-(2-hydroxy-3-phenoxypropylamino)ethoxy]phenoxyacetate (44.0 g) (the same starting material as in Example 2) and 2-methoxyethylamine (30 ml) were heated together on a steam-bath for 24 hours. The mixture was cooled and evaporated under reduced pressure to give an oily residue. This was dissolved in dichloromethane (200 ml) and treated with a solution of ether saturated with hydrogen chloride. The solvent was evaporated and the residual solid crystallised from a mixture of methanol and ethyl acetate to give (S)-4-[2-(2-hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide hydrochloride (39.2 g), m.p. 171°-3° C.; αD =-10.7° (c=1.0; methanol); microanalysis: found C, 58.1; H, 7.0; N, 6.0; Cl, 7.9%; required for C22H31ClN2O6 : C, 58.1; H, 6.9; N, 6.2; Cl 7.8%: NMR (DMSO-d6) 3.1(m,1H, CHCH2NH); 3.24(s, 3H,OCH3); 3.24-3.45(m,7H,CHCH2NHCH2 ; NHCH2CH2OCH3); 4.0(m,2H, ArOCH2CHOH); 4.2-4.35(m,3H,CHOH; CH2CH2OAr); 5.95(d,1H,OH); 6.85-7.05(m,7H,Ar); 7.3(m,2H,Ar); 8.15(t,1H, CONHCH2); 9.16 and 9.35 (broad peaks, 2H, NH2+).

Aufarbeitung

  1. temperaturewere heated together on a steam-bath for 24 hours
  2. temperatureThe mixture was cooled
  3. customevaporated under reduced pressure
  4. customto give an oily residue
  5. customThe solvent was evaporated
  6. customthe residual solid crystallised from a mixture of methanol and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c833be35e4444e50ba30f65e285e0347
Quelldatensatz
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04927836

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