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Diethylamine → Cyclopentyl(2S)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

HRID 425030
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 425030
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:18][C:19]#[CH:20])[C:10]([O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1.C(NCC)C>C(OCC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]#[C:19][CH2:18][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)=[O:11])=[CH:23][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8021DiethylamineHCID 115221-Bromo-4-iodobenzeneHCID 59243606cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

Produkt 1

HCID 59243578Cyclopentyl(2S)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodide
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a mixture of cyclopentyl(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate (2.45 g, 8.72 mmol) and 4-iodo-bromobenzene (2.96 g, 10.46 mmol) in diethyl ether (4 ml) was added copper iodide (0.166 g, 0.872 mmol) and PdCl2(PPh3)2 (0.306 g, 0.436 mmol). Diethylamine (5.43 ml, 52.3 mmol) was then added and the mixture stirred at RT. After 2 hrs, LCMS showed complete reaction. The mixture was poured onto water and extracted with diethyl ether. The combined organic layers were washed with water and brine, dried over magnesium sulphate, filtered and evaporated in vacuo. The crude residue was subjected to column chromatography eluting with 5 to 10% EtOAc in hexanes. Yield=2.9 g, 6.51 mmol, 75% yield. LCMS purity 98%: m/z 437 [M+H]+.

Aufarbeitung

  1. customreaction
  2. additionThe mixture was poured onto water
  3. extractionextracted with diethyl ether
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. washeluting with 5 to 10% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d37cb4d08d574798bbb03ca5e2fa5950
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106091B2

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