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Benzyl Bromide → Phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate

HRID 2367089
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2367089
[C:1]([CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[O:13])=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O.C(OCC)(=O)C>[N+:23]([C:7]1[CH:8]=[C:9]([C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([O:18][CH2:12][C:9]2[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=2)=[O:17])=[O:13])[CH:10]=[CH:11][C:6]=1[NH:5][CH2:4][C:1](=[O:3])[O:2][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O-:25])=[O:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 670441602-({4-[(Carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid

Produkt 1

HCID 67045250Phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoateAusbeute 165,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-({4-[(carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid (0.26 g, 0.76 mmol) in N,N-dimethyl formamide (5.0 mL), potassium carbonate (0.52 g, 3.80 mmol) was added, followed by the addition of benzyl bromide (0.22 mL, 1.82 mmol). The reaction mixture was stirred for 15 hours at room temperature. It was poured into ice water and diluted with ethyl acetate (50 mL). The organic layer was separated and it was washed with water, 2M aqueous hydrochloric acid and brine. It was dried over anhydrous sodium sulfate. Evaporating the solvent, followed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:1 to 3:2 eluent) resulted in phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate (0.33 g, 82% yield) as an amorphous residue. MS (EI) for C30H24N2O7: 524 (MH+).

Aufarbeitung

  1. customThe organic layer was separated
  2. washit was washed with water, 2M aqueous hydrochloric acid and brine
  3. dry with materialIt was dried over anhydrous sodium sulfate
  4. customEvaporating the solvent
  5. customfollowed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:1 to 3:2 eluent)

Quellen und Nachweise

ORD-Eintrag
ord-9a003baa69394a778ea1d36ddf63e88f
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697737B2

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