Sodium Hydroxide → HCID 19700602, Verbindung

HRID 1376652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376652
[Sn](Cl)Cl.[CH2:4]([O:6][C:7](=[O:32])[CH2:8][CH2:9][NH:10][C:11](=[O:31])[C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:13]=1[N+:28]([O-])=O)[CH3:5].C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(OCC)(=O)C.C(O)C.C(OCC)(=O)C>[CH2:4]([O:6][C:7](=[O:32])[CH2:8][CH2:9][NH:10][C:11](=[O:31])[C:12]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=2)[CH:15]=[CH:14][C:13]=1[NH2:28])[CH3:5]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 22905326HCID 22905326, Verbindung

Produkt 1

HCID 19700602HCID 19700602, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21584252Ethanol ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Tin(II) chloride (12.2 g, 64.4 mmol) was added to a solution of 5.12 g (12.9 mmol) of N-(5-(4-cyanobenzyloxy)-2-nitrobenzoyl)-b-alanine ethyl ester in 40 mL of 1:1 ethyl acetate/ethanol and the mixture heated to 70° C. for 15 min, cooled, and poured into a mixture of ice water, 1N sodium bicarbonate, and ethyl acetate. 1N sodium hydroxide was added carefully until a clear solution resulted and the aqueous phase was separated and extracted with ethyl acetate. The combined organics were washed with water, brine, dried over anhydrous magnesium sulfate, and concentrated to give a dark solid that was purified by chromatography (silica gel-60, 1:1 ethyl acetate/hexane) to give 2.51 g (53%) of N-(5-(4-cyanobenzyloxy)-2-aminobenzoyl)-b-alanine ethyl ester as a light yellow solid. 1H NMR (300 MHz, CDCl3) d 7.67 (2H, d, J=8.3 Hz, NC--Ar--H2), 7.52 (2H, d, J=8.3 Hz, NC--Ar--H2), 6.94 (1H, d, J=2.9 Hz, O--Ar--H), 6.89 (1H, dd, J=2.9, 8.8 Hz, O--Ar--H), 6.78 (1H, b, N--H), 6.66 (1H, d, J=8.8 Hz, O--Ar--H), 5.04 (2H, s, ArCH2O), 4.16 (2H, q, J=7.3 Hz, OCH2CH3), 3.66 (2H, bq, J=5.8 Hz, NHCH2CH2), 2.62 (2H, t, J=5.8 Hz, NHCH2CH2), 1.27 (3H, t, J=7.3 Hz, OCH2CH3); Exact mass (FAB, M+H+) calcd for C20H22N3O4 : 368.1610; Found: 368.1603.

Aufarbeitung

  1. temperaturecooled
  2. customresulted
  3. customthe aqueous phase was separated
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a dark solid
  9. customthat was purified by chromatography (silica gel-60, 1:1 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b9f0899ffc114f088047c0894273bd66
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663166

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