Hydrochloric Acid → benzhydryl (2R)-hydroxy-4-phenylbutyrate

HRID 274237

Reaktionsgleichung

Reaktionsgleichung von HRID 274237
[OH:1][C@H:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Li+].Cl.[C:19]1([C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N+]=[N-])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[OH:1][C@H:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 2733848Ethyl (R)-2-hydroxy-4-phenylbutyrate

Produkt 1

HCID 54145254benzhydryl (2R)-hydroxy-4-phenylbutyrateAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dissolve (R)-2-hydroxy-4-phenylbutyric acid, ethyl ester (4.16 g, 20 mmol) in methanol (40 mL). Add 1N lithium hydroxide (25 mL, 25 mmol) and stir under an atmosphere of argon for 3.5 hours. Acidify with 1N hydrochloric acid (25 mL), saturate with sodium chloride and extract with ethyl acetate (3×25 mL). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Take up the residue in methylene chloride (20 mL) and add diphenyldiazomethane (3.36 g, 17.3 mmol). Stir overnight and wash with saturated sodium hydrogen carbonate (2×). Dry (MgSO4), evaporate the solvent in vacuo and recrystallize (methylene chloride/hexane then again with cyclohexane) to give (R)-2-hydroxy-4-phenylbutyric acid, diphenylmethyl ester as white needles (2.3 g, 38%); mp 82°-84° C.

Aufarbeitung

  1. concentrationsaturate with sodium chloride
  2. extractionextract with ethyl acetate (3×25 mL)
  3. dry with materialCombine the organic phases, dry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. stirringStir overnight
  6. washwash with saturated sodium hydrogen carbonate (2×)
  7. dry with materialDry (MgSO4)
  8. customevaporate the solvent in vacuo
  9. customrecrystallize (methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-377c9589bc794dde8794dfeef371643d
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389628

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