StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → HCID 178472444, Verbindung

HRID 1087649
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1087649
[C:1]([O:5][C:6](=[O:33])[CH:7]([CH2:17][N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8][C:9]1([C:14](O)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.[CH2:64]([O:66][C:67]([C@H:69]1[CH2:74][CH2:73][C@@H:72]([NH2:75])[CH2:71][CH2:70]1)=[O:68])[CH3:65]>ClCCl>[C:1]([O:5][C:6](=[O:33])[CH:7]([CH2:17][N:18]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8][C:9]1([C:14](=[O:15])[NH:75][C@H:72]2[CH2:71][CH2:70][C@@H:69]([C:67]([O:66][CH2:64][CH3:65])=[O:68])[CH2:74][CH2:73]2)[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:3])([CH3:4])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 221554593-(1-Carboxycyclopentyl)-2(dibenzylaminomethyl)propanoic acid t-butyl esterHCID 178472435HCID 178472435, Verbindung

Produkt 1

HCID 178472444
HCID 178472444, Verbindung
Ausbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The t-butyl ester from step (b) above (11.97 g, 26.54 mmole) in dry dichloromethane (200 ml), under nitrogen, was treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.19 g, 53 mmole), 1-hydroxybenztriazole (3.94 g, 29 mmole), triethylamine (16.08 g, 22.15 ml, 159 mmole) and cis-4-aminocyclohexane-carboxylic acid ethyl ester hydrochloride (6.04 g, 20 mmole). After stirring overnight at room temperature, the solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with dilute hydrochloric acid (2x), dilute aqueous sodium bicarbonate, water, dried (Na2SO4) and evaporated to yield the crude product (15.5 g). This was chromatographed on silica (400 g) eluting with 1 to 10% diethyl ether in dichloromethane. Evaporation of the desired fractions gave 3-{1-[(cis-4-ethoxycarbonyl-cyclohexyl)-carbamoyl]cyclopentyl}-2-(dibenzylaminomethyl)propanoic acid t-butyl ester as an oil (11.43 g, 71%). Found: C,73.38; H,8.87; N,4.42. C37H52N2O5 requires: C,73.48; H,8.67; N,4.68%.

Aufarbeitung

  1. customthe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with dilute hydrochloric acid (2x), dilute aqueous sodium bicarbonate, water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto yield the crude product (15.5 g)
  7. customThis was chromatographed on silica (400 g)
  8. washeluting with 1 to 10% diethyl ether in dichloromethane
  9. customEvaporation of the desired fractions

Quellen und Nachweise

ORD-Eintrag
ord-2d0fd8d8926a41729c52460b39f21006
Quelldatensatz
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05036104

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion