Diisopropylethylamine → 2-(4-Fluorophenyl)propionic acid

HRID 476230

Reaktionsgleichung

Reaktionsgleichung von HRID 476230
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=N[C:10]1=2)=[N+](C)C)C.[F:18][P-](F)(F)(F)(F)F.CCN(C(C)C)[CH:28]([CH3:30])[CH3:29].CN[C@H]1CN2C3C(C(C[C:49]([O:51]CCC)=[O:50])=C2CC1)=CC=CC=3>CN(C=O)C>[F:18][C:29]1[CH:14]=[CH:13][C:12]([CH:11]([CH3:10])[C:49]([OH:51])=[O:50])=[CH:30][CH:28]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86655417propyl [(7R)-7-(methylamino)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate

Produkt 1

HCID 27239152-(4-Fluorophenyl)propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

(33 mg) and HATU (76 mg) were dissolved in DMF (1.3 mL). DIPEA (87 μL, 0.315 mmol) was added and the mixture was stirred for 1 min before the addition of propyl [(7R)-7-(methylamino)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate (50 mg) in 1 mL DMF. The reaction mixture was stirred for 2 h. The solvent was removed under vacuum and the residue was purified on silica gel (ethyl acetate/hexanes). The resulting diastereoisomers were separated on a Chiralpak AD column (20% iPrOH/Hexanes, 0.25% HCOOH). The propyl esters were hydrolysed to their corresponding acids using a procedure analogous to the one described in Step 2. MS (+ESI) m/z: 409.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified on silica gel (ethyl acetate/hexanes)
  3. customThe resulting diastereoisomers were separated on a Chiralpak AD column (20% iPrOH/Hexanes, 0.25% HCOOH)

Quellen und Nachweise

ORD-Eintrag
ord-2e430c3310ff4cfc95166c1f0f1e9cc4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637671B2

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