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Ethyl Acetate → Methyl 2-((3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propoxy)methyl)-benzoate

HRID 1429362
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1429362
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([CH2:17][OH:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].CC(=O)OCC>C1COCC1>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:19])[CH2:17][O:18][CH2:23][C:24]2[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:15][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 57594209tert-Butyl 3-(4-bromophenyl)-1-hydroxypropan-2-ylcarbamate

Produkt 1

HCID 67382431Methyl 2-((3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propoxy)methyl)-benzoateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of compound 3f (6.6 g, 20 mmol) in dry THF (100 mL) was added NaH (60%, 960 mg, 24 mmol) in small portions at 0° C. and stirred for 1 hr. Then compound 3b (5 g, 22 mmol) in THF (50 mL) was added dropwise, and the reaction mixture was allowed to stir at rt overnight. The reaction was quenched with water and extracted with EA (2×100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by CC eluting with PE:EA=9:1 to give 3g as a white solid (3.2 g, 34% yield).

Aufarbeitung

  1. stirringto stir at rt overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with EA (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by CC
  7. washeluting with PE

Quellen und Nachweise

ORD-Eintrag
ord-1a31c6c7eb334efba815538644671012
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08940722B2

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