Lithium Hydroxide → 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

HRID 1189568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189568
[OH:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:26][C:27]([O:29]CC)=[O:28])[C:6]([CH3:25])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]=1[CH3:9].[Li+].[OH-]>C1COCC1.CO.O>[OH:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:26][C:27]([OH:29])=[O:28])[C:6]([CH3:25])=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)(=[O:18])=[O:19])=[CH:13][CH:12]=2)[C:8]=1[CH3:9]

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 58310958ethyl 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

Produkt 1

HCID 583109212-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acidAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Ethyl 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (20 mg, 0.045 mmol) in THF (2.0 ml), MeOH (0.500 ml) and water (0.50 ml) was stirred and LiOH (4.27 mg, 0.178 mmol) was added. The resulting mixture was stirred at 25° C. for two hours. The solvent was then removed and water was added, followed by 1 N HCl. The solvent was again removed, MeOH was added, and the resulting solution purified by preparative HPLC to give 12 mg of a light blue solid (12 mg, 0.029 mmol, 64.0% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.63 (d, 2H), 7.19 (d, 2H), 4.57 (s, 2H), 3.76 (s, 2H), 3.66 (t, 2H), 3.18-3.15 (m, 4H), 2.76-2.73 (m, 4H), 2.03 (s, 3H), 1.78 (s, 3H), 1.70-1.66 (m, 4H).

Aufarbeitung

  1. customThe solvent was then removed
  2. additionwater was added
  3. customThe solvent was again removed
  4. additionMeOH was added
  5. customthe resulting solution purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-78aa3118824d4cd684cbb70d3c1a26c9
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674115B2

Notizen zur Reaktion

Wird geladen…