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Triethylamine → (3S)-3-(benzyloxy)-N-methoxy-N-methylbutanamide

HRID 238945
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238945
[CH2:1]([O:8][C@@H:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH2:1]([O:8][C@@H:9]([CH3:14])[CH2:10][C:11]([N:17]([O:18][CH3:19])[CH3:16])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11845529(S)-3-(Benzyloxy)butanoic acid

Produkt 1

HCID 86658651
(3S)-3-(benzyloxy)-N-methoxy-N-methylbutanamide
Ausbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, to a solution of the above (3S)-3-(benzyloxy)butanoic acid (225 g) in DMF (1.5 L), N,O-dimethylhydroxylamine hydrochloride (111 g, 1.1 mol) and triethylamine (0.32 mL, 2.3 mol) were added, and the mixture was stirred at room temperature for 40 minutes. Subsequently, 1-hydroxybenzotriazole (112 g, 0.83 mol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (160 g, 0.83 mol) were successively added, and the mixture was stirred at room temperature for 5 hours. After the reaction, the reaction mixture was poured to ice-water, and it was extracted with diethyl ether. After it was successively washed with 1N hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, it was dried with sodium sulfate and the solvent was distilled off under reduced pressure to give (3S)-3-(benzyloxy)-N-methoxy-N-methylbutanamide (196 g) as a mixture. The present compound was used for the subsequent reaction without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. customAfter the reaction
  3. extractionwas extracted with diethyl ether
  4. washAfter it was successively washed with 1N hydrochloric acid, water
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, it was dried with sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e7a1ba0f82484c3cab1353d64f3faac4
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642640B2

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