Hydrochloric Acid → HCID 58813133, Verbindung

HRID 1391708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391708
[Li+].[OH-].[CH2:3]([C@H:7]1[CH2:11][CH2:10][N:9]([C@@H:12]([CH2:17][CH:18]=[CH2:19])[C:13]([O:15]C)=[O:14])[C:8]1=[O:20])[CH2:4][CH2:5][CH3:6].Cl>O.C1COCC1>[CH2:3]([C@H:7]1[CH2:11][CH2:10][N:9]([C@@H:12]([CH2:17][CH:18]=[CH2:19])[C:13]([OH:15])=[O:14])[C:8]1=[O:20])[CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58813147(S)-methyl 2-((S)-3-butyl-2-oxopyrrolidin-1-yl)pent-4-enoate

Produkt 1

HCID 58813133HCID 58813133, VerbindungAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step B (5): A solution of LiOH (2 M, 69 mg, 2.9 mmol) in 1.4 mL of H2O was added to diastereomer A, (S)-methyl 2-((S)-3-butyl-2-oxopyrrolidin-1-yl)pent-4-enoate, (242 mg, 0.96 mmol) from Step B (4) in THF (1.4 mL). The reaction mixture was stirred at room temperature for 3 days. The mixture was poured into 1 N HCl and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over NaSO4 and concentrated in vacuo to give 182 mg of (S)-2-((S)-3-butyl-2-oxopyrrolidin-1-yl)pent-4-enoic acid as colorless oil: LC-MS (M+H)+=240.2; 1H NMR (500 MHz, CDCl3) δ 5.60-5.82 (m, 1H), 5.03-5.21 (m, 2H), 4.74 (dd, J=10.68, 4.88 Hz, 1H), 3.38-3.48 (m, 1H), 3.29-3.38 (m, 1H), 2.70-2.81 (m, 1H), 2.51-2.62 (m, 1H), 2.36-2.49 (m, 1H), 2.11-2.25 (m, 1H), 1.79-1.91 (m, 1H), 1.66-1.79 (m, 1H), 1.23-1.43 (m, 5H), 0.80-0.96 (m, 3H).

Aufarbeitung

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3657a0cb924d470a9b43b16f46c5c621
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338974B2

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