Sodium Carbonate → (2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 890577

Reaktionsgleichung

Reaktionsgleichung von HRID 890577
Cl.C[O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.Cl[S:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O.CN(C)C=O.ClCCl.C(N(CC)CC)C.N1C=CC=CC=1>[S:12]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:4]([OH:3])=[O:10])([C:15]1[CH:23]=[CH:22][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Komponenten

10

Edukt 4

HCID 10340Sodium CarbonateHCID 823854-(Chlorosulfonyl)benzoic acidHCID 2733200methyl L-prolinate hydrochlorideHCID 4327891Pentafluorophenyl Trifluoroacetate

Produkt 1

HCID 691957(2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

N-tosyl-proline derivatives were synthesized as follows. Proline methyl ester hydrochloride was reacted with 4-(chlorosulfonyl)benzoic acid and sodium carbonate in water. The product was converted to the pentafluorophenyl ester by reacting it with pentafluorophenyl trifluoroacetate and pyridine in N,N-dimethylformamide, and purified via flash chromatography. This activated ester was then reacted with the methyl-ester of glutamate (or any of the other amino acids tested) in the presence of triethylamine and dichloromethane, the product purified by flash chromatography, and the methyl esters hydrolyzed with lithium hydroxide in water. The final products were purified via reverse-phase HPLC and lyophilized.

Aufarbeitung

  1. custompurified via flash chromatography
  2. customThis activated ester was then reacted with the methyl-ester of glutamate (or any of the other amino acids
  3. customthe product purified by flash chromatography
  4. customThe final products were purified via reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9f53c9452f294edf8695ae1906d4800c
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06998233B2

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