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

Benzyl Alcohol → 1-Tert-butyl 3-ethyl (3R,4S)-4-{[(benzyloxy)carbonyl]amino}pyrrolidine-1,3-dicarboxylate

HRID 456258
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 456258
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.CC[N:48]([CH:52](C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10]([NH:48][C:52](=[O:36])[O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11437663rac-(3R,4R)-1-[(tert-butoxy)carbonyl]-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid

Produkt 1

HCID 701984471-Tert-butyl 3-ethyl (3R,4S)-4-{[(benzyloxy)carbonyl]amino}pyrrolidine-1,3-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (3S*,4S*)-1-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid (see Example 12, Step 2) (7.01 g, 24.4 mmol), benzyl alcohol (3.16 g, 29.15 mmol), diphenylphosphoryl azide (8.06 g, 29.3 mmol) and DIPEA (3.76 g, 29.15 mmol) in toluene (320 mL) was stirred at 80° C. for 15 hours. The toluene was partially evaporated, water was added and the mixture was extracted with CHCl3. The combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 5→15% MeOH in CHCl3 giving the title product.

Aufarbeitung

  1. customThe toluene was partially evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with CHCl3
  4. dry with materialThe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 5→15% MeOH in CHCl3 giving the title product

Quellen und Nachweise

ORD-Eintrag
ord-febe6d192b034b3a913f539bb79d281d
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08497383B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion