L-Hydroxyproline → (2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid

HRID 458332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458332
[NH:1]1[CH2:9][C@H:7]([OH:8])[CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(N1CCOCC1)C.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C[Si](C)(C)N[Si](C)(C)C.C1COCC1.CCOCC.C(O)C>[OH:8][C@H:7]1[CH2:9][N:1]([S:28]([C:19]2[CH:20]=[CH:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)(=[O:30])=[O:29])[C@H:2]([C:3]([OH:5])=[O:4])[CH2:6]1

Komponenten

9

Edukt 4

HCID 5810L-HydroxyprolineHCID 71252-Naphthalenesulfonyl chlorideHCID 7525EthylmorpholineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 6363699(2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acidAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 13838HexamethyldisilazaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

11 g (83.9 mmol) L-Hydroxyproline were dissolved in 110 ml hexamethyldisilazane and heated to 120° C. overnight, cooled to room temperature and evaporated. The oily residue was dissolved in 110 ml THF, 16.5 ml (79.7 mmol, 0.95 eq) N-ethyl-morpholine was added, followed by 18.25 g (79.7 mmol, 0.95 eq) 2-naphthalenesulfonyl chloride in 130 ml THF over a period of 60 min. The solution was stirred at RT for 50 h, 15 ml ethanol were added and the solution was stirred for 15 min. At that time 400 ml of Et2O and 250 ml of aqueous saturated NaHCO3 solution were added and the phases were separated. The aqueous layer was acidified and extracted with EtOAc, the combined organic layers were washed with brine, dried over MgSO4 and concentrated. 17.39 g (65%) (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid isolated as yellow solid, mp 140° C., MS: 321 (MH+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customevaporated
  3. dissolutionThe oily residue was dissolved in 110 ml THF
  4. stirringthe solution was stirred for 15 min
  5. customthe phases were separated
  6. extractionextracted with EtOAc
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cea5cdd3e803416589ea81d494012952
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189756B2

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