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Potassium Phosphate, Tribasic → tert-Butyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}pyridin-3-yl)carbamate

HRID 1481294
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1481294
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH:10]=[CH2:11])[CH:3]=1.[C:20]([O:24][C:25]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:33]=1B(O)O)=[O:26])([CH3:23])([CH3:22])[CH3:21].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[C:15]([O:14][C:13]([NH:12][C@H:8]([C:4]1[CH:3]=[C:2]([C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[NH:27][C:25](=[O:26])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:7]=[CH:6][N:5]=1)[CH2:9][CH:10]=[CH2:11])=[O:19])([CH3:18])([CH3:17])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 15366412(3-((tert-Butoxycarbonyl)amino)pyridin-4-yl)boronic acidHCID 66744734Carbamic acid, N-[(1S)-1-(4-chloro-2-pyridinyl)-3-buten-1-yl]-, 1,1-dimethylethyl ester

Produkt 1

HCID 131736624tert-Butyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}pyridin-3-yl)carbamateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To 1C (1.080 g, 3.82 mmol) and (3-((tert-butoxycarbonyl)amino)pyridin-4-yl)boronic acid (1 g, 4.20 mmol) in a sealable flask was added THF (19.09 ml), potassium phosphate tribasic (5.09 ml, 15.28 mmol) and degassed with Ar. (DtBPF)PdCl2 (0.249 g, 0.382 mmol) was added, degassed further. The reaction mixture was heated at 75° C. for overnight. Then, the mixture was washed with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, concentrated and purified by ISCO to yield 72A as brown solid (670 mg, 40%). 1H NMR (500 MHz, METHANOL-d4) δ 8.65 (br. s., 1H), 8.62-8.57 (m, 1H), 8.46 (d, J=5.0 Hz, 1H), 7.46 (s, 1H), 7.41 (d, J=5.2 Hz, 1H), 7.39 (m, 1H), 5.86-5.75 (m, 1H), 5.15-5.03 (m, 2H), 4.81-4.75 (m, 1H), 2.68-2.57 (m, 1H), 2.55-2.46 (m, 1H), 1.46-1.27 (m, 18H).

Aufarbeitung

  1. customdegassed with Ar
  2. customdegassed further
  3. washThen, the mixture was washed with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by ISCO

Quellen und Nachweise

ORD-Eintrag
ord-64b87fdc8e9b48239d5912f4bd06e57b
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409908B2

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