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Propargyl alcohol → HCID 20205910, Verbindung

HRID 543237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 543237
[C:1]([NH:9][CH:10]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](O)[C:25]#[CH:26].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH:9][CH:10]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:11]([O:13][CH2:26][C:25]#[CH:24])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7859Propargyl alcoholHCID 10868DicyclohexylcarbodiimideHCID 2948912-benzamido-3-(1H-indol-3-yl)propanoic acid

Produkt 1

HCID 20205910HCID 20205910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(benzoylamino)-3-(indol-3-yl)propanoic acid (1.9 g) was dissolved in 75 ml of dry methylene chloride (from phosphorous pentoxide). The solution was cooled to 0° C. in an ice bath and 0.72 ml of propargyl alcohol was added along with 1.39 g of DCC followed by 0.07 g DMAP. The reaction mixture was warmed to room temperature and maintained there for 16 hours. The solution was filtered into a separatory funnel, washed with 5% acetic acid (2×), water (1×) and 5% solution bicarbonate (1×). The separated methylene chloride layer was then dried over magnesium sulfate and evaporated to dryness. The residue was redissolved in ethyl acetate, filtered and the filtrate evaporated to dryness. The orangish residue was dried in vacuo to give propargyl 2-(benzoylamino)-3-(indol-3-yl)propionate.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperaturemaintained there for 16 hours
  3. filtrationThe solution was filtered into a separatory funnel
  4. washwashed with 5% acetic acid (2×), water (1×) and 5% solution bicarbonate (1×)
  5. dry with materialThe separated methylene chloride layer was then dried over magnesium sulfate
  6. customevaporated to dryness
  7. dissolutionThe residue was redissolved in ethyl acetate
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness
  10. customThe orangish residue was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1d38b6c30064478e9f634029882ea6d5
Quelldatensatz
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04661510

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