Sodium Hydroxide → (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid

HRID 1994079

Reaktionsgleichung

Reaktionsgleichung von HRID 1994079
C([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:35])[C:12]([CH3:34])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH:15]=1)[CH3:13])=[O:5])C.[OH-].[Na+]>CO.O>[CH3:34][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH:15]=1)([CH3:13])[C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@@H:6]1[C:4]([OH:5])=[O:3])=[O:35]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 68675740(R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester

Produkt 1

HCID 11362875(R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of title D compound, (R)-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid ethyl ester (0.47 g, 0.99 mmol) in methanol (25 mL) is added sodium hydroxide (0.16 g, 3.95 mmol) in water (5 mL) at RT. The reaction mixture is stirred for 16 h. The reaction mixture is concentrated at reduced pressure, poured into water, the aqueous layer is separated, washed with ethyl acetate twice, acidified with concentrated HCl and extracted three times with ethyl acetate. The combined ethyl acetate extract is dried and concentrated to give (R)-1-{2-methyl-2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionyl}-pyrrolidine-2-carboxylic acid as a white solid: MS m/z 447.3 [M−1]−.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated at reduced pressure
  2. additionpoured into water
  3. customthe aqueous layer is separated
  4. washwashed with ethyl acetate twice
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined ethyl acetate extract
  7. customis dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f9b55db6907457499864929752d2d34
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652061B2

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