Hydrochloric Acid → (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoic acid
Reaktionsgleichung
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:14]([O:17][C@@H:18]([CH2:20][CH2:21][CH:22]=[CH2:23])[CH3:19])[CH2:15][CH3:16])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li+].[OH-].Cl>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:14]([O:17][C@@H:18]([CH2:20][CH2:21][CH:22]=[CH2:23])[CH3:19])[CH2:15][CH3:16])[C:10]([OH:12])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a round-bottom flask equipped with a stir bar was added (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate (458 mg, 1.39 mmol), THF (5 mL) and MeOH (5 mL). To the stirred solution was added aq. LiOH (2.0 M, 2 mL). The mixture was stirred for 16 h, then was concentrated in vacuo to afford an aqueous solution. The solution was acidified with aq. HCl (1 M) and then transferred to a separatory funnel. The mixture was twice extracted with EtOAc. The combined organics were washed with brine; dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoic acid as a white foam (438 mg, 100%).
Aufarbeitung
- customTo a round-bottom flask equipped with a stir bar
- concentrationwas concentrated in vacuo
- customto afford an aqueous solution
- customtransferred to a separatory funnel
- extractionThe mixture was twice extracted with EtOAc
- washThe combined organics were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationthen concentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-53382597b4f846c6979d990b718d94f0
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09334279B2
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