Lithium hydroxide, monohydrate → (S)-2-(N-methylhexanamido)pent-4-enoic acid

HRID 501669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501669
[Li+].[OH-].O.[CH3:4][N:5]([C@@H:13]([CH2:18][CH:19]=[CH2:20])[C:14]([O:16]C)=[O:15])[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C1COCC1>[CH3:4][N:5]([C@@H:13]([CH2:18][CH:19]=[CH2:20])[C:14]([OH:16])=[O:15])[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 86622310(S)-methyl 2-(N-methylhexanamido)pent-4-enoate

Produkt 1

HCID 59423702(S)-2-(N-methylhexanamido)pent-4-enoic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step F (3): According to the general procedure outlined in Step A (3), a solution of LiOH/H2O (2M, 2.5 mL), was added to a mixture of (S)-methyl 2-(N-methylhexanamido)pent-4-enoate (254 mg, 1.05 mmol) in THF (2.5 mL) to afford 229 mg (96% yield) of (S)-2-(N-methylhexanamido)pent-4-enoic acid as a clear viscous oil. LC-MS (M+H)+=228.2; 1H NMR (500 MHz, CDCl3) δ ppm 0.82-0.93 (m, 3H) 1.23-1.36 (m, 4H) 1.55-1.70 (m, 2H) 2.26-2.38 (m, 2H) 2.47-2.59 (m, 1H) 2.71-2.80 (m, 1H) 2.94 (s, 3H) 4.99-5.19 (m, 3H) 5.61-5.75 (m, 1H) 5.91 (br s, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-f3da2cedf7e143afb84ba2ae2038351a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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