Ammonium Chloride → (3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

HRID 1677091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677091
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]([N:17]1[C@H:22]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=2)[CH2:21][O:20][CH2:19][C@@H:18]1[C@H:32]([OH:34])[CH3:33])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>C(OCC)(=O)C.C(N(CC)CC)C.O1CCCC1.CS(C)=O>[CH2:7]([O:14][C:15]([N:17]1[C@H:22]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=2)[CH2:21][O:20][CH2:19][C@@H:18]1[C:32](=[O:34])[CH3:33])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

8

Edukt 3

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 67373415(3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

Produkt 1

HCID 67372176(3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl esterAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A tetrahydrofuran solution (15 mL) of dimethyl sulfoxide (0.22 mL) was cooled to −78° C., and oxalyl chloride (246 μL) was added dropwise into the resultant solution. The reaction solution was stirred for 5 minutes at the same temperature, and a tetrahydrofuran (5 mL) solution of (3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorphenyl)morpholin-4-carboxylic acid benzyl ester (880 mg) was added dropwise. The resultant reaction solution was stirred for 1 hour at the same temperature, and triethylamine (1.54 mL) was added. The reaction solution was returned to room temperature, and stirring was continued for 1 hour. Ammonium chloride aqueous solution and ethyl acetate were added to the reaction solution, and the organic layer was partitioned, and the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the resultant was purified by silica gel column chromatography (heptane/ethyl acetate), and the title compound (800 mg) was obtained. The physical property values are as follows.

Aufarbeitung

  1. customThe resultant reaction solution
  2. additionwas added
  3. customwas returned to room temperature
  4. stirringstirring
  5. waitwas continued for 1 hour
  6. customthe organic layer was partitioned
  7. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  8. customThe solvent was removed under a vacuum
  9. customthe resultant was purified by silica gel column chromatography (heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4bd99c254a3a48b6bebc5166a2f22a96
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008293B2

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