Benzyl chloroformate → (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 431752

Reaktionsgleichung

Reaktionsgleichung von HRID 431752
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1.O.C1COCC1>[OH:1][C@H:2]1[CH2:6][N:5]([C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:21])[C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 440014Cis-4-Hydroxy-D-Proline

Produkt 1

HCID 688416(2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A suspension of cis4-hydroxy-D-proline (10.0 g) in THF-water (1:1, 100 mL) was added 1N NaOH solution (50 mL) at 5° C. To the mixture was added a solution of benzyloxycarbonyl chloride (12.5 mL) in THF (10 mL) keeping pH to 8.5-10 by the addition of 2N NaOH solution at 5-10° C. After stirring at the same temperature for 1 h, the reaction mixture was washed with EtOAc (50 mL), adjusted to pH 2 by the addition of 4N HCl, and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and evaporated in vacuo to give cis4-hydroxy-N-benzyloxycarbonyl-D-proline (18.74 g).

Aufarbeitung

  1. washthe reaction mixture was washed with EtOAc (50 mL)
  2. additionadjusted to pH 2 by the addition of 4N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-051f27377594404abecb19039afecd8c
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660759B1

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