Lithium hydroxide, monohydrate → L-Valine, 3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-

HRID 659823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659823
[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([C:16]([O:18]C)=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:6].O[Li].O>CO.O>[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([C:16]([OH:18])=[O:17])[NH:4][C:5]([O:7][C@@H:8]1[CH2:10][C@H:9]1[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])=[O:6]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59287267L-Valine,3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-,methyl ester

Produkt 1

HCID 59287076L-Valine, 3-methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution (0.1 M) of methyl 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valinate in 2:1 mixture of MeOH/H2O was treated with LiOH.H2O (4 eq) and then heated at 60° C. for 4 h. The mixture was cooled and concentrated to half volume, then diluted with EtOAc and acidified with aqueous HCl (1 N). The organic layer was separated and washed with brine then dried. Removal of the volatiles afforded the title compound (98%) as an oil. MS (ES+) m/z 284 (M+H)+

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to half volume
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customthen dried
  7. customRemoval of the volatiles

Quellen und Nachweise

ORD-Eintrag
ord-ca269026d3d5484fa82d96005a14e377
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080654B2

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