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Water → HCID 57635145, Verbindung

HRID 1971088
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1971088
[CH3:1][C:2]([CH3:30])([CH3:29])[C@H:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:21]#[C:22][C:23]2[CH:28]=[CH:27]C=CC=2)[N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5].C1(B(O)O)CCCC=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.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>[C:21]1([C:13]2[N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][C:15]3=[C:11]([C:9]([NH:8][C@@H:3]([C:2]([CH3:1])([CH3:29])[CH3:30])[C:4]([NH:6][CH3:7])=[O:5])=[O:10])[N:12]=2)[CH2:27][CH2:28][CH2:23][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 57635127HCID 57635127, Verbindung

Produkt 1

HCID 57635145HCID 57635145, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Compound 203 (100 mg, 0.26 mmol) was dissolved in dioxane (2 mL) and cyclopentenylboronic acid (58 mg, 0.52 mmol) was added, followed by potassium carbonate (72 mg, 0.52 mmol) and water (0.40 mL). The resulting solution was degassed with nitrogen gas and Pd(PPh3)4 (18 mg, 0.016 mmol) was added. The mixture was heated at 100° C. for 1 h under nitrogen. The organic layer was separated, solid NaCl was added and the mixture was extracted with ethyl acetate. The combined organic layers were filtered through PL-Thiol MP SPE tube to remove palladium catalyst. The filtrate was concentrated and then purified by prep LC/MS using 5-95% acetonitrile in water with 0.1% formic acid. The formic acid was removed using Strata SCX SPE tube to give a desired product (Compound 238) as a free base (81 mg, 82%). 1H-NMR (400 MHz, CDCl3) δ: 1.09 (s, 9H), 1.90-2.05 (m, 2H), 2.51 (s, 3H), 2.55-2.65 (m, 2H), 2.74-2.95 (m, 7H), 3.88-4.14 (m, 4H), 5.95 (s, 1H), 6.09 (m, 1H), 7.66 (d, 1H). LCMS (+ESI) m/z 374.2 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. customThe organic layer was separated
  3. additionsolid NaCl was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. filtrationThe combined organic layers were filtered through PL-Thiol MP SPE tube
  6. customto remove palladium catalyst
  7. concentrationThe filtrate was concentrated
  8. custompurified by prep LC/MS
  9. customThe formic acid was removed

Quellen und Nachweise

ORD-Eintrag
ord-1c95e78ed8fa42959f048c31da372b3d
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08431565B2

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