Sodium Bicarbonate → (S)-methyl 5-[1-(2-phenylthiazol-4-yl)-2-(4-nitrophenyl)-ethylamino]thiazole-4-carboxylate

HRID 60049

Reaktionsgleichung

Reaktionsgleichung von HRID 60049
CC(C)([O-])C.[K+].[N+:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])#[C-:8].[C:14]1([C:20]2[S:21][CH:22]=[C:23]([C@@H:25]([N:36]=[C:37]=[S:38])[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)[N:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>C1COCC1>[C:14]1([C:20]2[S:21][CH:22]=[C:23]([C@@H:25]([NH:36][C:37]3[S:38][CH:8]=[N:7][C:9]=3[C:10]([O:12][CH3:13])=[O:11])[CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)[N:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 547815Methyl isocyanoacetateHCID 23665647Potassium tert-butoxideHCID 57841130(S)-2-phenyl-4-(1-isothiocyanato-2-(4-nitrophenyl)ethyl)thiazole

Produkt 1

HCID 59464674(S)-methyl 5-[1-(2-phenylthiazol-4-yl)-2-(4-nitrophenyl)-ethylamino]thiazole-4-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of potassium tert-butoxide (89 mg, 0.75 mmol) in THF (3 mL) is added methyl isocyanoacetate (65 μL, 0.68 mmol) followed by (S)-2-phenyl-4-(1-isothiocyanato-2-(4-nitrophenyl)ethyl)thiazole, 43, (250 mg, 0.68 mmol). The reaction mixture is stirred at room temperature for 2 hours then poured into sat. NaHCO3. The mixture is extracted with EtOAc (3×25 mL) and the combined organic layers are washed with brine and dried (Na2SO4) and concentrated in vacuo. The crude residue is purified over silica to afford 323 mg (˜100% yield) of the desired product as a slightly yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.09-8.13 (m, 2H), 7.95-7 98 (m, 3H), 7.84 (d, J=1.2 Hz, 1H), 7.44-7.50 (m, 3H), 7.28-7.31 (m, 2H), 7.96 (d, J=0.6 Hz, 1H), 4.71-4.78 (m, 1H), 3.92 (s, 3H), 3.60 (dd, J=13.8 and 6.0 Hz, 1H), 3.45 (dd, J=13.8 and 6.0 Hz, 1H).

Aufarbeitung

  1. extractionThe mixture is extracted with EtOAc (3×25 mL)
  2. washthe combined organic layers are washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is purified over silica

Quellen und Nachweise

ORD-Eintrag
ord-9dea8102be3d4f50985f3e3421de251d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440963B2

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