1-Piperazinecarboxylic acid, ethyl ester → 4-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1185444

Reaktionsgleichung

Reaktionsgleichung von HRID 1185444
[C:1]([O:5][C:6](=[O:23])[CH2:7][C@H:8]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:46]([O:48][C:49]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)=[O:50])[CH3:47].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:46]([O:48][C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:9](=[O:11])[C@@H:8]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:23])[CH2:55][CH2:56]1)=[O:50])[CH3:47]

Komponenten

6

Edukt 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 669202694-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 25 g of (S)-2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester, 35.6 g of NEM and 25.3 g of TOTU in 125 ml of DMF, 12.9 g of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 3 h. The reaction mixture was diluted saturated aqueous sodium hydrogen carbonate solution and extracted with 400 ml of ethyl acetate. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1). The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 35.4 g.

Aufarbeitung

  1. extractionextracted with 400 ml of ethyl acetate
  2. washThe organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1)
  6. additionThe fractions containing the product
  7. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a353c04b1cfd4b909f7c6f2e9469fe64
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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