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

Nitrogen → [1-(5-Hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 2064913
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2064913
N#N.C[O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[CH:17]=[C:16]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[O:20])[CH:15]=[N:14]2)=[CH:10][CH:11]=1)=O.[BH4-].[Na+]>CO>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][O:21][C:19](=[O:20])[NH:18][C:16]1[CH:15]=[N:14][N:13]([CH2:12][C:9]2[O:8][C:7]([CH2:5][OH:4])=[CH:11][CH:10]=2)[CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 33347405-[4-(2-Chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-furan-2-carboxylic acid methyl esterHCID 4311764Sodium borohydride

Produkt 1

HCID 66928887[1-(5-Hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-[4-(2-chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-furan-2-carboxylic acid methyl ester (3.30 g, 8.46 mmol) in MeOH (33.0 mL) was treated portionwise, at rt with NaBH4 (3.33 g, 84.60 mmol). The reaction mixture was stirred at rt overnight before being quenched by pouring in sat. aq. NH4Cl (100 mL), extracted with EA (3×100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:70 hept-EA) gave the title compound. TLC: rf (30:70 hept-EA)=0.22. LC-MS-conditions 02: tR=0.86 min; [M+H]+=362.32. 1H NMR (400 MHz, CDCl3) δ 2.94 (s, 1H), 4.52 (s, 2H), 5.15 (s, 2H), 5.28 (s, 2H), 6.21 (s, 1H), 6.28 (s, 1H), 7.04 (s, 1H), 7.22-7.35 (m, 2H), 7.35 (s, 1H), 7.35-7.46 (m, 2H), 7.69 (s, 1H).

Aufarbeitung

  1. custombefore being quenched
  2. additionby pouring in sat. aq. NH4Cl (100 mL)
  3. extractionextracted with EA (3×100 mL)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (30:70 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-ab83fba18fc64b72b1e12192f452bde3
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08288419B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion