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

Potassium Phosphate, Tribasic → HCID 178495674, Verbindung

HRID 1751611
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1751611
[CH3:1][CH:2]([CH3:39])[C@H:3]([NH:34][C:35](=[O:38])[O:36][CH3:37])[C:4](=[O:33])[N:5]1[C@H:10]([C:11]2[NH:15][C:14]3[C:16]4[C:21]([CH:22]=[CH:23][C:13]=3[N:12]=2)=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][CH:17]=4)[CH2:9][C@@H:8]2[C@H:6]1[CH2:7]2.Br[C:41]1[CH:42]=[C:43]2[C:66](=[CH:67][CH:68]=1)[C:47]1[NH:48][C:49]([C@@H:51]3[CH2:55][C@H:54]([CH2:56][O:57][CH3:58])[CH2:53][N:52]3[C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])=[N:50][C:46]=1[CH:45]=[CH:44]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:37][O:36][C:35]([NH:34][C@@H:3]([CH:2]([CH3:1])[CH3:39])[C:4]([N:5]1[C@H:10]([C:11]2[NH:15][C:14]3[C:16]4[C:21]([CH:22]=[CH:23][C:13]=3[N:12]=2)=[CH:20][C:19]([C:41]2[CH:42]=[C:43]3[C:66](=[CH:67][CH:68]=2)[C:47]2[NH:48][C:49]([C@@H:51]5[CH2:55][C@H:54]([CH2:56][O:57][CH3:58])[CH2:53][N:52]5[C:59]([O:61][C:62]([CH3:65])([CH3:63])[CH3:64])=[O:60])=[N:50][C:46]=2[CH:45]=[CH:44]3)=[CH:18][CH:17]=4)[CH2:9][C@@H:8]2[C@H:6]1[CH2:7]2)=[O:33])=[O:38]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 178495670HCID 178495670, VerbindungHCID 178502481HCID 178502481, Verbindung

Produkt 1

HCID 178495674HCID 178495674, VerbindungAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl (S)-3-methyl-1-oxo-1-((1R,3S,5R)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[3.1.0]hexan-2-yl)butan-2-ylcarbamate (0.60 g, 1.1 mmol) and (2S,4S)-tert-butyl 2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate (0.46 g, 1.0 mmol) in DME (5 mL) was added Pd(PPh3)4 (0.08 g, 0.07 mmol) and K3PO4 (2M aqueous, 1.5 mL, 3.0 mmol). The resulting solution was degassed with argon for 5 min and heated to 80° C. (external temperature, oil bath) for 18 h. The reaction mixture was then cooled to room temperature and diluted with MeOH and CH2Cl2. The solution was washed with H2O and brine, and the aqueous layers were back extracted with CH2Cl2 and MeOH (˜10:1). The organic layers were combined and dried over Na2SO4 and concentrated. The crude oil was purified by silica gel chromatography (30 to 100% EtOAc (10% MeOH)/Hexanes to 80% MeOH/EtOAc) to provide (2S,4S)-tert-butyl 2-(2′-((1R,3S,5R)-2-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-2-azabicyclo[3.1.0]hexan-3-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate (0.79 g, 71%). LCMS-ESI+: calc'd for C45H51N7O6: 785.39 (M+); Found: 786.61 (M+H+).

Aufarbeitung

  1. customThe resulting solution was degassed with argon for 5 min
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. additiondiluted with MeOH and CH2Cl2
  4. washThe solution was washed with H2O and brine
  5. extractionthe aqueous layers were back extracted with CH2Cl2 and MeOH (˜10:1)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude oil was purified by silica gel chromatography (30 to 100% EtOAc (10% MeOH)/Hexanes to 80% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d75496a3785e4582b8bb8146b4a1f0ac
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156823B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion