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

Tetrahydrofuran → (2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester

HRID 1527377
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1527377
OC(C(F)(F)F)=O.[CH2:8]([O:15][C:16]([C@@H:18]1[CH2:22][C@@H:21]([F:23])[CH2:20][NH:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:24]([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36]([NH2:38])=[O:37])[CH:28]=1)=[C:25]=[O:26].C1COCC1.C(N(CC)CC)C>O>[CH2:8]([O:15][C:16]([C@@H:18]1[CH2:22][C@@H:21]([F:23])[CH2:20][N:19]1[C:25](=[O:26])[NH:24][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36](=[O:37])[NH2:38])[CH:28]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 575200853-Isocyanato-indole-1-carboxylic acid amideHCID 131733200(2S,4R)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester TFA salt

Produkt 1

HCID 68283894(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (2S,4R)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester TFA salt (4.45 g, 13.2 mmol), 3-isocyanato-indole-1-carboxylic acid amide (2.65 g, 13.2 mmol) (prepared as described in Scheme A1) and THF (66 mL) was added triethylamine (5.51 mL, 39.6 mmol). The resulting solution was stirred at RT under nitrogen for 1 h until completion of the reaction. The mixture was poured in water and extracted with EtOAc. The organic layer was washed with an aqueous saturated solution of NaHCO3, dried over Na2SO4, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1 to pure EtOAc) to give the desired compound. TLC, Rf (CH2Cl2/MeOH 9:1)=0.40; MS: 425.2 [M+H]+; tR (HPLC conditions a): 3.6 min.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with an aqueous saturated solution of NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1 to pure EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2501bf94a0854a1d849c33a6cdf8d32e
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09085555B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion