Lithium hydroxide, monohydrate → HCID 42597521, Verbindung

HRID 1664111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664111
[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]([CH:24]=[C:25]4[C:30]=2[CH:29]=[CH:28][CH:27]=[CH:26]4)=[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:12]=[CH:13][C:14]([C:17]2[C:18]3[C:23]([CH:24]=[C:25]4[C:30]=2[CH:29]=[CH:28][CH:27]=[CH:26]4)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 42597519Methyl (2S)-2-acetamido-3-(4-[9-anthracenyl]phenyl)-propanoate

Produkt 1

HCID 42597521HCID 42597521, VerbindungAusbeute 900 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

To a solution of 96 (80 mg, 0.02 mmol) in THF/water, 2:1 (3 mL) was added lithium hydroxide monohydrate (17 mg, 0.40 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 (69 mg, 0.18 mmol, 90%) as a white solid. Mp 76° C. [α]D20 +29.7 (c. 0.1, EtOH). 1H NMR (CDCl3, 300 MHz): δ 8.47 (s, 1H, ArH10″); 8.02 (d, J=8.4 Hz, 2H, ArH3″ and ArH6″); 7.59 (d, J=8.7 Hz, 2H, ArH8″ and ArH1″); 7.45 (m, 2H, ArH4″ and ArH5″); 7.35 (m, 6H, ArH2″ and ArH7″, 4×ArH′); 6.27 (d, J=6.6 Hz, 1H, NH); 5.00 (m, 1H, H2); 3.39 (dd, J=4.8, 12.9 Hz, 1H, H3a); 3.26 (dd, J=6.3, 14.4 Hz, 1H, H3b); 2.07 (s, 3H, COCH3). Mass Spectrum (ES, +ve) m/z 383 (70%) [MH+]. HRMS calcd for C25H22NO3 384.1600, found 384.1610.

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-ced1a66edad74b0da840c0d1d17a189d
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039430B2

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