Citric Acid → (S)-1-((Benzyloxy)carbonyl)pyrazolidine-3-carboxylic acid

HRID 1396837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396837
[N:1]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5][CH2:4][C@@H:3]([C:6]([O:8]C)=[O:7])[NH:2]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[C:14]1([CH2:13][O:12][C:10]([N:1]2[CH2:5][CH2:4][C@@H:3]([C:6]([OH:8])=[O:7])[NH:2]2)=[O:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 311Citric AcidHCID 594155711-Benzyl 3-methyl (S)-pyrazolidine-1,3-dicarboxylate

Produkt 1

HCID 68287653(S)-1-((Benzyloxy)carbonyl)pyrazolidine-3-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl 1-(phenylmethyl) (3S)-1,3-pyrazolidinedicarboxylate (2.77 g, 10.5 mmol) in THF (20 mL) at 0° C. was added a portion of LiOH monohydrate. The mixture was warmed up to rt and stirred for 2 hours. TLC showed that the starting material was consumed completely. THF was distilled off, and the mixture was cooled to 0° C. Citric acid (4.8 g, 25.2 mmol) in water (20 mL) was then added dropwise. The aqueous mixture was extracted with DCM (8×20 mL), the combined organic phases were dried (Na2SO4), filtered and concentrated to provide (3S)-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid as yellowish solid (1.8 g, 83%). 1H NMR (300 MHz, DMSO-D6) δ 7.43-7.29 (m, 5H), 5.07 (s, 2H), 3.76-3.71 (m, 1H), 3.52-3.37 (m, 2H), 2.25-2.06 (m, 2H).

Aufarbeitung

  1. customwas consumed completely
  2. distillationTHF was distilled off
  3. temperaturethe mixture was cooled to 0° C
  4. extractionThe aqueous mixture was extracted with DCM (8×20 mL)
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af83d757289a4856b9103d63ac51f685
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901119B2

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