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Methanol → 3-{5-[1-Hydroxy-3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-methyl-2-phenoxy-propionic acid methyl ester

HRID 585273
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 585273
[CH3:1][O:2][C:3](=[O:35])[C:4]([CH3:34])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:5][C:6]1[S:7][C:8]([C:11](=[O:26])[CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])=[CH:9][CH:10]=1.CO.[BH4-].[Na+].CCOC(C)=O>C1COCC1.CCCCCC>[CH3:1][O:2][C:3](=[O:35])[C:4]([CH3:34])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:5][C:6]1[S:7][C:8]([CH:11]([OH:26])[CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:17][C:18]=2[CH3:19])=[CH:9][CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 208231592-Methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propionyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester

Produkt 1

HCID 208231613-{5-[1-Hydroxy-3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-methyl-2-phenoxy-propionic acid methyl ester
Ausbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A sample of 2-methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propionyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester (1.00 g, 2.04 mmol) was dissolved in THF (40 mL) and MeOH (20 mL) and cooled to 0° C. Sodium borohydride (115 mg, 3.06 mmol) was added and allowed to stir at. 0° C. for 45 min. The reaction was monitored by HPLC. Upon the completion of the reaction, the bulk of the solvent was removed in vacuo and water (40 mL) was added. The mixture was acidified with 6 N HCl (20 mL) and stirred for 30 min. This aqueous mixture was then extracted with CH2Cl2 (2×50 mL). The organic fractions were combined, dried over NaCl, and solvent removed in vacuo to give a crude oil. Flash chromatography (gradient 20% to 40% EtOAc in hexane) provided 650 mg (65%) of desired product: 1H NMR (400 MHz, CDCl3) δ 8.02 (d, 2H), 7.47 (m, 3H), 7.19 (m, 2H), 6.96 (t, 1H), 6.79 (m, 3H), 6.68 (d, 2H), 4.96 (m, 1H), 3.72 (s, 3H), 3.43 (d, 1H), 3.29 (d, 1H), 2.71 (m, 2H), 2.30 (s, 3H), 2.17 (m, 2H), 1.42 (s, 3H); MS (EI) 492.2 (M+H)+.

Aufarbeitung

  1. customUpon the completion of the reaction
  2. customthe bulk of the solvent was removed in vacuo and water (40 mL)
  3. additionwas added
  4. stirringstirred for 30 min
  5. extractionThis aqueous mixture was then extracted with CH2Cl2 (2×50 mL)
  6. dry with materialdried over NaCl, and solvent
  7. customremoved in vacuo
  8. customto give a crude oil

Quellen und Nachweise

ORD-Eintrag
ord-e1853ccd39464287baa157c7188613af
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06930120B2

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