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

HRID 1510281

반응식

HRID 1510281 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-11e1bfed13414a8a8a01e05d7cb11878
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211914B2

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