Lithium hydroxide, monohydrate → [({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acid

HRID 1350249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350249
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][N:25]([CH2:27][C:28]([O:30]CC)=[O:29])[CH3:26])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O>O1CCOCC1.O>[C:15]([O:14][C:12](=[O:13])[CH2:11][C@H:10]([C:19]1[O:23][N:22]=[C:21]([CH2:24][N:25]([CH2:27][C:28]([OH:30])=[O:29])[CH3:26])[N:20]=1)[CH2:9][CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 60077674tert-butyl(3R)-6-cyclohexyl-3-(3-{[(2-ethoxy-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Produkt 1

HCID 60077601[({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acidAusbeute 120,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl(3R)-6-cyclohexyl-3-(3-{[(2-ethoxy-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate (preparation 132) (1.00 g, 2.21 mmol) in dioxan (20 ml) and H2O (20 ml) was treated with LiOH.H2O (193 mg, 2.21 mmol) and the reaction mixture stirred at room temperature for 19 hours. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with brine. The aqueous was extracted with EtOAc (×3). The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure to afford the title compound as a white foam (1.13 g).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with brine
  4. extractionThe aqueous was extracted with EtOAc (×3)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3652e746ce4c4dd1b8c7b53772f43b4a
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214694B2

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