Hydroxypyridinone → Fmoc-D-Hyp-Gly-OtBu

HRID 374370

Reaktionsgleichung

Reaktionsgleichung von HRID 374370
[N:1]1([C:10]([O:12][CH2:13][CH:14]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:9][C@@H:7]([OH:8])[CH2:6][C@@H:2]1[C:3](O)=[O:4].[NH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].ON1C=CC=CC1=O.F[B-](F)(F)F.C(C(=NOC(N(C)C)=[N+](C)C)C(OCC)=O)#N.C(N(C(C)C)CC)(C)C>C(#N)C.CN(C=O)C>[N:1]1([C:10]([O:12][CH2:13][CH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:11])[CH2:9][C@@H:7]([OH:8])[CH2:6][C@@H:2]1[C:3]([NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:4]

Komponenten

8

Edukt 5

HCID 69975HydroxypyridinoneHCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7408199(2R,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 131717656Fmoc-D-Hyp-Gly-OtBu

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.4 g of Fmoc-D-Hyp-OH are dissolved in 25 ml of dry acetonitrile and then 1.05 g of H-Gly-OtBu and 0.445 g of N-hydroxypyridone are added. Then 1.31 g of O-[(cyano(ethoxycarbonyl)methylidene)amino]-1,1,3,3-tetramethyluronium tetrafluoroborate (TOTU) are introduced in/portions within 10 minutes, as well as 1.03 ml of diisopropylethylamine in 15 ml of DMF dropwise over the course of 15 minutes. After 1 h, the mixture is concentrated, the residue is taken up in ethyl acetate and extraction with sodium chloride solution is carried out. The organic phase is dried over sodium sulfate and evaporated to dryness. The remaining oil is taken up in a little ether and added dropwise to petroleum ether while stirring. The flocculent precipitate is filtered off with suction and dried in vacuo.

Aufarbeitung

  1. customdropwise over the course of 15 minutes
  2. concentrationthe mixture is concentrated
  3. extractionextraction with sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated to dryness
  6. additionadded dropwise to petroleum ether
  7. filtrationThe flocculent precipitate is filtered off with suction
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1c72ccf168904bfabd7b4c73a04aa3e8
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166394

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