N-(tert-butoxycarbonyl)glycine → Tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate

HRID 1465454

Reaktionsgleichung

Reaktionsgleichung von HRID 1465454
[Br:1][C:2]1[CH:10]=[CH:9][C:5](NCC)=[CH:4][CH:3]=1.[C:11]([NH:18][CH2:19][C:20]([OH:22])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Cl.[CH2:24]([N:26]=C=NCCCN(C)C)[CH3:25].C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]([NH:18][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:20]([NH:26][CH2:24][CH3:25])=[O:22])=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117456564-bromo-N-ethylaniline

Produkt 1

HCID 86651843Tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-N-ethylaniline (1.28 g, 6.4 mmol), N-Boc-glycine (1.57 g, 9.0 mmol) in pyridine (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.47 g, 7.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 hrs. The reaction mixture was poured into a mixture of diluted aqueous sodium hydrogen carbonate solution and ethyl acetate. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate (2.255 g, yield 99%) as a yellow solid.

Aufarbeitung

  1. stirringThe mixture was stirred
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-25a144044dc44926b0ad03b5e4a7d73f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999989B2

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