Trifluoroacetic acid → Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetate

HRID 1616998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616998
[CH2:1]([O:8][C:9](=[O:12])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13](O)([C:15](F)(F)F)=[O:14].[C:20]([O:24][C:25](=[O:31])NCC(=O)N)([CH3:23])([CH3:22])[CH3:21].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9](=[O:12])[CH2:10][NH:11][C:13](=[O:14])[CH2:15][C:25]([O:24][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 409140Benzyl glycinateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109100641,1-Dimethylethyl N-(2-amino-2-oxoethyl)carbamate

Produkt 1

HCID 68088972Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetateAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Benzyl-2-aminoacetate, TFA salt (13; 1.72 g, 5.12 mmol) and carbamoylmethyl-carbamic acid tert-butyl ester (8a; 1.13 g, 6.19 mmol) were dissolved in 40 mL dichloromethane with stirring at 0° C., followed by addition of N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDC; 1.33 g, 7.0 mmol) and triethylamine (1.0 mL, 7.2 mmol), and the reaction was replaced under room temperature with continuous stirring for 6 h. After the reaction was completed, dichloromethane was removed by concentration under reduced pressure. The obtained solid was dissolved in ethyl acetate (50 mL), and then the organic phase was washed by H2O, 5% citric acid, H2O, saturated NaHCO3 and saturated NaCl solution separately, and dried over MgSO4 and concentrated under reduced pressure to remove ethyl acetate to obtain colorless oil-like 14 (1.15 g; 72.6%). 1H-NMR (200 MHz) (CDCl3) δ: 7.28-7.33 (m, 5H, ArH), 6.89 (br, s, 1H, CONHCH2), 5.36 (br, s, 1H, NHBOC), 5.13 (s, 2H, CO2CH2Ph), 4.04 (d, 2H, CH2CO2CH2Ph), 3.81 (d, 2H, CH2NHBOC), 1.40 [s, 9H, CO2C(CH3)3].

Aufarbeitung

  1. customwas replaced under room temperature
  2. stirringwith continuous stirring for 6 h
  3. customdichloromethane was removed by concentration under reduced pressure
  4. dissolutionThe obtained solid was dissolved in ethyl acetate (50 mL)
  5. washthe organic phase was washed by H2O, 5% citric acid, H2O, saturated NaHCO3 and saturated NaCl solution separately
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto remove ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d8b039c8ed704d629c795cd32c898d27
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765934B2

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