1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide

HRID 2086240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086240
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:21][C:20]1=[O:35].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[CH2:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][N:19]([NH:18][C:15](=[O:17])[CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)[C:20](=[O:35])[CH2:21]1)=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 22727156Benzyl 4-amino-3-oxopiperazine-1-carboxylate

Produkt 1

HCID 22727280N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamideAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of 1-(tert-butoxycarbonyl)-4-piperidinylacetic acid (440 mg), 1-amino-4-benzyloxycarbonyl-2-piperazinone (541 mg), triethylamine (273 mg) and HOBt (333 mg) in DMF (30 ml) was combined with WSC (518 mg) and stirred at room temperature for 15 hours. The reaction mixture was concentrated to obtain a residue, which was partitioned between ethyl acetate and water, and the organic phase was washed with water, aqueous sodium bicarbonate, an aqueous solution of citric acid and brine, dried and concentrated to obtain N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide (840 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto obtain a residue, which
  3. customwas partitioned between ethyl acetate and water
  4. washthe organic phase was washed with water, aqueous sodium bicarbonate
  5. dry with materialan aqueous solution of citric acid and brine, dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa833f15517747bc9a31649cb8ba8585
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723722B1

Notizen zur Reaktion

Wird geladen…