Triethylamine → Methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate

HRID 891054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891054
Cl.[NH2:2][CH:3]([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>ClCCl>[OH:9][CH2:8][CH:3]([NH:2][C:23]([C:22]1[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:27][CH:26]=1)=[O:24])[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 517373Methyl DL-serinate hydrochloride

Produkt 1

HCID 22064268Methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl 2-amino-3-hydroxypropanoate hydrochloride (L-serine methyl ester hydrochloride, 1.71 g, 11 mmol) was stirred in dichloromethane (20 ml) at 0° C., and triethylamine (2.79 ml, 20 mmol) added, followed by dropwise addition of 4-trifluoromethylbenzoyl chloride (1.486 ml, 11 mmol). The mixture was stirred at 0° C. for 30 minutes, then partitioned between dichloromethane and water, dried over magnesium sulfate, and filtered. Solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography, to yield methyl 3-hydroxy-2-{[4-(trifluoromethyl)phenyl]carbonylamino}propanoate, a compound of formula (13). B. Preparation of a Compound of Formula (14)

Aufarbeitung

  1. custompartitioned between dichloromethane and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customSolvent was removed from the filtrate under reduced pressure
  5. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7ca61d0d3fb642459c353aa366c0e7a8
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001909B2

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