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Lithium Hydroxide → 2-Tert-butoxy-2-[4-(2,4-dimethylphenyl)-7-[1-(2-hydroxyethyl)triazol-4-yl]-2-methyl-1-oxo-3-isoquinolyl]acetic acid

HRID 572533
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572533
[C:1]([O:5][CH:6]([C:11]1[N:12]([CH3:32])[C:13](=[O:31])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])=[CH:18][CH:17]=[C:16]([C:29]#[CH:30])[CH:15]=2)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].C([O:36][CH2:37][CH2:38][N:39]=[N+:40]=[N-:41])(=O)C.O=C1O[C@H]([C@H](CO)O)C(O)=C1O.[OH-].[Li+]>C(O)C.O.C(OCC)(=O)C.CO.O1CCCC1.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:4][C:1]([O:5][CH:6]([C:11]1[N:12]([CH3:32])[C:13](=[O:31])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])=[CH:18][CH:17]=[C:16]([C:29]1[N:41]=[N:40][N:39]([CH2:38][CH2:37][OH:36])[CH:30]=1)[CH:15]=2)[C:7]([OH:9])=[O:8])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 4

HCID 3939Lithium HydroxideHCID 120185192-Azidoethyl acetateHCID 54670067L-Ascorbic AcidHCID 86700725Methyl 2-(tert-butoxy)-2-(4-(2,4-dimethylphenyl)-7-ethynyl-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate

Produkt 1

HCID 715962962-Tert-butoxy-2-[4-(2,4-dimethylphenyl)-7-[1-(2-hydroxyethyl)triazol-4-yl]-2-methyl-1-oxo-3-isoquinolyl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 61499Cupric sulfate monohydrateKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of methyl 2-(tert-butoxy)-2-(4-(2,4-dimethylphenyl)-7-ethynyl-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate (26.0 mg, 0.060 mmol), 2-azidoethyl acetate (10.11 mg, 0.078 mmol), ascorbic acid (2.123 mg, 0.012 mmol) and copper sulfate monohydrate (1.923 mg, 0.012 mmol) in Ethanol (1.2 mL) and Water (0.2 mL) was irradiated in the microwave at 120° C. for 10 minutes. The mixture was diluted with ethyl acetate, then washed with saturated sodium bicarbonate and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The resulting crude residue in methanol (1.0 mL), tetrahydrofuran (THF) (1.0 mL) and water (0.2 mL) was treated with lithium hydroxide (28.8 mg, 1.205 mmol) and then heated to 60° C. for 90 minutes. The mixture was concentrated to dryness, water was added and the mixture was adjusted to pH 3-4 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate; the extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase chromatography to afford the desired product as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) (atropisomers) δ=8.75-8.54 (m, 1 H), 8.14 (br. s., 2 H), 7.43 (d, J=7.6 Hz, 1 H), 7.15 (d, J=14.6 Hz, 2 H), 7.04-6.85 (m, 1 H), 5.44-5.15 (m, 1 H), 4.56 (m, 2 H), 4.14 (m, 2 H), 3.83-3.64 (m, 3 H), 2.43 (s, 3 H), 2.15-1.83 (m, 3 H), 1.29-0.97 (m, 9 H); LC/MS (m/z) ES+=505 (M+1).

Aufarbeitung

  1. customwas irradiated in the microwave at 120° C. for 10 minutes
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationThe mixture was concentrated to dryness, water
  7. additionwas added
  8. extractionThe mixture was extracted with ethyl acetate
  9. washthe extracts were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-307a6aa1080f4d0ea4725fce8f491eae
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029391B2

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