Hexadecane → N-(2-Phenylacetyl)-4-Keto-D,L-Proline Methyl Ester

HRID 583007

Reaktionsgleichung

Reaktionsgleichung von HRID 583007
[CH3:1][O:2][C:3](=[O:19])[C@H:4]1[CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:10](=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.COC(=O)[C@@H]1CC(=O)CN1C(=O)CC1C=CC=CC=1.CCCCCCCCCCCCCCCC>C([O-])(=O)C.[Na+].ClCCl>[CH3:1][O:2][C:3](=[O:19])[CH:4]1[CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:10](=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 11006HexadecaneHCID 53997628N-(2-phenylacetyl)-4-keto-D-proline methyl esterHCID 53997629N-(2-phenylacetyl)-4-keto-L-proline methyl ester

Produkt 1

HCID 21226264N-(2-Phenylacetyl)-4-Keto-D,L-Proline Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 517045Sodium AcetateLösungsmittel

Versuchsvorschrift

An aqueous solution (1.0 mL) containing 19 mM of N-(2-phenylacetyl)-4-keto-D-proline methyl ester and 19 mM of N-(2-phenylacetyl)-4-keto-L-proline methyl ester in 0.200M sodium acetate (pH 5.0) and 25 mg/mL of Candida antartica lipase fraction B was mixed at 25° C. The reaction mixture was analyzed by mixing with an equivalent volume of 20 mM hexadecane in dichloromethane for 3 minutes, which resulted in the complete extraction of the unreacted D- and L-isomers. The dichloromethane extract was then analyzed by chiral gas chromatography on a Chiraldex G-TA column (Advanced Separation Technologies, Inc., 50 m×0.32 mm ID) to determine the relative amounts of the unreacted D- and L-isomers. After 28 h, 97% of the D-isomer and 28% of the L-isomer remained, yielding a 55% enantiomeric excess of the D-isomer at 38% conversion of the racemic mixture (E=28).

Aufarbeitung

  1. additionwas mixed at 25° C
  2. customwhich resulted in the complete extraction of the unreacted D- and L-isomers
  3. extractionThe dichloromethane extract
  4. customwas then analyzed by chiral gas chromatography on a Chiraldex G-TA column (Advanced Separation Technologies, Inc., 50 m×0.32 mm ID)
  5. customyielding a 55% enantiomeric excess of the D-isomer at 38% conversion of the racemic mixture (E=28)

Quellen und Nachweise

ORD-Eintrag
ord-5495bc3290b2416f89e7039bb9585889
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05928933

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