Triethylamine → 4-{4-[(2-Phenyl-5-ethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1510281

Reaktionsgleichung

Reaktionsgleichung von HRID 1510281
[C:1]1([C:7]2[O:8][C:9]([CH2:15][CH3:16])=[C:10]([C:12]([OH:14])=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CS(C)=O.CCOC(C)=O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:12]([C:10]3[N:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:8][C:9]=3[CH2:15][CH3:16])=[O:14])=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 150939472-Phenyl-5-ethyl-oxazole-4-carboxylic acidHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Produkt 1

HCID 674396964-{4-[(2-Phenyl-5-ethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-phenyl-5-ethyl-oxazole-4-carboxylic acid (180 mg, 0.829 mmol), 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (218 mg, 0.79 mmol), triethylamine (467 mL, 3.316 mmol), and BOP (366 mg, 0.89 mmol) in 5 mL DMSO was stirred at room temperature for 1.0 hr. The reaction was taken up in EtOAc (50 mL) and washed with hydrochloric acid (0.1N, 20 mL), water (20 mL), saturated sodium bicarbonate solution (20 mL), and brine (20 mL). The organic layer was dried with anhydrous magnesium sulfate and filtered to give 4-{4-[(2-phenyl-5-ethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester. ES-MS for C28H33N3O4 calcd. (m/e) 47.5, observed 476 (M−H).

Aufarbeitung

  1. washwashed with hydrochloric acid (0.1N, 20 mL), water (20 mL), saturated sodium bicarbonate solution (20 mL), and brine (20 mL)
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-11e1bfed13414a8a8a01e05d7cb11878
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211914B2

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