Carbon Dioxide → (2R)-2-methyl-3-phenylpropanoic acid

HRID 546335

Reaktionsgleichung

Reaktionsgleichung von HRID 546335
C(N)(C)(C)C.[CH3:6][C@@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9].C(=O)=O.C1(/C(=C\C2C=CC=CC=2)/C(O)=O)C=CC=CC=1>CO>[CH3:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 700620alpha-Phenylcinnamic acid, (E)-HCID 24786872(s)-2-Methyl-3-phenylpropionic acid tert-butylamine salt

Produkt 1

HCID 5287791(2R)-2-methyl-3-phenylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(S)-2-Methyl-3-phenylpropionic acid tert-butylamine salt, reaction time 40 minutes, conversion 100%, ee 96.5% (SFC, 2× Chiralpak AD-H columns, 10% methanol, 3000 psi CO2, 35° C., flow rate 3 ml/minute, retention times R 7.1 minutes, S 7.7 minutes, (E)-phenylcinnamic acid 12 minutes). The free acid was liberated by partitioning between dichloromethane and 2M HCl. The organic layer was dried (Na2SO4), filtered and the solvent was evaporated to give (R)-2-Methyl-3-phenylpropionic acid as a pale yellow solid. [α]D20+98.6, c=2.03, CHCl3. [α]D20+100.6, c=0.54, acetone. [α]D20+103.5 (c=1.00, MeOH). Lit. (M. B. Watson and G. W. Youngson, J. Chem. Soc. C, 1968, 258-261; +140.8, c=2.04, CHCl3). 1H NMR analysis of the (S)-methyl mandelate (E. Tyrell, M. W. H. Tang, G. A. Skinner and J. Fawcett, Tetrahedron, 1996, 52, 9841-9852) confirmed assignment of (S)-configuration.

Aufarbeitung

  1. customby partitioning between dichloromethane and 2M HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-848b56a50cf74721a64e14d6dee48019
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935841B2

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