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Hydrochloric Acid → rac-2-[(3R,4R)-4-(carboxymethyl)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidin-3-yl]acetic acid

HRID 634995
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 634995
[CH2:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]([OH:16])=[O:15])[C@H:10]([CH2:17][C:18]([OH:20])=[O:19])[CH2:9]1)C1C=CC=CC=1.[C:21]([O-:24])([O-])=O.[Na+].[Na+].ClC(OC[C:32]1[C:44]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][CH:33]=1)=O.Cl.C([OH:48])C>O.O1CCOCC1.C1(C)C=CC=CC=1.[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][C:14]([OH:16])=[O:15])[C@H:10]([CH2:17][C:18]([OH:20])=[O:19])[CH2:9]1)([O:24][CH2:21][CH:43]1[C:44]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:48]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 14261773Fluorenylmethyl chloroformateHCID 70229250N-Benzyl-trans-3,4-bis-(Carboxymethyl)-Pyrrolidine

Produkt 1

HCID 70229222
rac-2-[(3R,4R)-4-(carboxymethyl)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}pyrrolidin-3-yl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

N-Benzyl-trans-3,4-bis-(Carboxymethyl)-Pyrrolidine is dissolved in ethanol, and a catalytic amount of 10% Pd/C is added. The suspension is shaken under 3 atm H2 overnight. The catalyst is filtered, the solvent removed and the residue and Na2CO3 (1.3 eq) are suspended in H2O/Dioxane (1:1) (0.1M). Fluorenylmethyl chloroformate (1.1 eq) in toluene is added dropwise. The temperature of the reaction is not allowed to rise above 25° C. during the addition. The mixture is stirred vigorously overnight, acidified to pH 3 with conc HCl, and extracted twice with ethyl acetate. The organic extract is washed with brine, dried with MgSO4, filtered and the solvent removed in vacuo. The product is purified by chromatography.

Aufarbeitung

  1. filtrationThe catalyst is filtered
  2. customthe solvent removed
  3. additionto rise above 25° C. during the addition
  4. stirringThe mixture is stirred vigorously overnight
  5. extractionextracted twice with ethyl acetate
  6. extractionThe organic extract
  7. washis washed with brine
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customThe product is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-48750bb2f4304feea2fbb06373a6dac8
Quelldatensatz
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06184389B2

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