Lithium hydroxide, monohydrate → HCID 42597522, Verbindung

HRID 1664112

Reaktionsgleichung

Reaktionsgleichung von HRID 1664112
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH:30]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.O>[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH:30]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 42597520Methyl (2S)-2-acetamido-3-(4-[9-phenanthrenyl]phenyl)propanoate

Produkt 1

HCID 42597522HCID 42597522, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 98 (124 mg, 0.31 mmol) in THF/water, 2:1 (9 mL) was added lithium hydroxide monohydrate (26 mg, 0.62 mmol) and the resulting suspension was allowed to stir for 16 h. The reaction mixture was diluted with water (30 mL) and the THF was removed by evaporation. The aqueous layer was washed with DCM (40 mL) to remove unreacted starting material. The aqueous phase was acidified with 10% HCl and the resulting precipitate was extracted with DCM (3×40 mL). The combined organics were dried and evaporated to yield the title compound (65 mg, 0.17 mmol, 55%) as a white solid. Mp 128-132° C. [α]D20 +36.8 (c. 0.1, EtOH). 1H NMR (CD3OD, 300 MHz): δ 8.71 (d, J=8.1 Hz, 1H, ArH4″); 8.66 (d, J=8.4 Hz, 1H, ArH3″); 7.79 (s, 1H, ArH1″); 7.76 (s, 1H, ArH10″); 7.51 (m, 5H, ArH7″, ArH6″, ArH5″, ArH2″ and ArH1″); 7.32 (m, 2H, Ar′H); 4.76 (dd, J=5.1, 9.0 Hz, 1H, H2); 3.29 (dd, J=4.8, 13.5 Hz, 1H, H3a); 3.03 (dd, J=8.7, 13.5 Hz, 1H, H3b); 1.95 (s, 3H, COCH3). Mass Spectrum (ES, +ve) m/z 384 (50%) [MH+]. HRMS calcd for C25H22NO3 384.1600, found 384.1628.

Aufarbeitung

  1. customthe THF was removed by evaporation
  2. washThe aqueous layer was washed with DCM (40 mL)
  3. customto remove unreacted
  4. extractionthe resulting precipitate was extracted with DCM (3×40 mL)
  5. customThe combined organics were dried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-81e143deb3b541d39b28898d0bf91b8b
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039430B2

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