Hydrochloric Acid → Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid

HRID 1160938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160938
C[O:2][C:3](=[O:42])[CH2:4][CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:22][C:23]2[C:28]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][C:26]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:25][C:24]=2[C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>O1CCCC1.C(OCC)C.O>[C:29]([C:28]1[CH:27]=[C:26]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:25]=[C:24]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:23]=1[O:22][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[O:41])=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:19])[F:20])([CH3:31])([CH3:32])[CH3:30]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67153635Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid methyl ester

Produkt 1

HCID 67153428Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Racemic 3-{4-[1-(2,4,6-tri-t-butyl-phenoxy)-5,5,5-trifluoro-pentyl]-benzoylamino}-propionic acid methyl ester (0.333 g, 0.500 mmol) is dissolved in tetrahydrofuran (3.0 mL) and sodium hydroxide (3.0 mL, 5N) is added. The reaction is monitored by HPLC, and upon complete conversion, the reaction is neutralized with hydrochloric acid (3.0 mL, 5N) and diluted with diethyl ether and water. The two phases are separated, and the organic layer is washed, dried, and concentrated. The title compound is used without further purification. MS (ES): 652.2 [M−H]−.

Aufarbeitung

  1. customThe two phases are separated
  2. washthe organic layer is washed
  3. customdried
  4. concentrationconcentrated
  5. customThe title compound is used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-36b049eadb73442f858e6efa6e1fafe3
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816557B2

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