Aniline → (S)-tert-butyl 1-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate

HRID 571996ノート

反応式

HRID 571996 の反応式
P([O-])(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH2:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:19]=1[C:20]([OH:22])=O.[C:28]([O:32][C:33]([NH:35][C@@H:36]([CH3:40])[C:37](O)=O)=[O:34])([CH3:31])([CH3:30])[CH3:29].[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>N1C=CC=CC=1.CCOC(C)=O>[Cl:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:18]2[C:19]=1[C:20](=[O:22])[N:41]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:37]([C@@H:36]([NH:35][C:33](=[O:34])[O:32][C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:40])=[N:17]2

参加物

7

反応物 4

HCID 6115AnilineHCID 750712-Amino-6-chlorobenzoic acidHCID 85082Tert-butoxycarbonylalanineHCID 23418553Diphenoxyphosphanolate

生成物 1

HCID 86686186(S)-tert-butyl 1-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

Diphenyl phosphite (1.9 mL, 10 mmol) was added to a solution of 2-amino-6-chlorobenzoic acid (495 mg, 2.9 mmol) and (S)-2-(tert-butoxycarbonylamino)propanoic acid (710 mg, 3.77 mmol) in pyridine (3 mL). The reaction mixture was stirred at 40° C. for 2 hours. Aniline (274 mg, 3.48 mmol) was then added to the reaction mixture, which was then stirred at 55° C. for 12 hours. The reaction mixture was cooled to room temperature. This mixture was then diluted with EtOAc (50 mL), washed with 1N aqueous HCl (2×50 mL), brine (50 mL), and dried over sodium sulfate. The organics layer was filtered and concentrated in vacuuo to afford material which was purified by column chromatography on SiO2 eluting with EtOAc in hexanes (0-50%) to afford (S)-tert-butyl 1-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate as a solid. ES/MS m/z=400.1 (M+H+).

後処理

  1. stirringwas then stirred at 55° C. for 12 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with 1N aqueous HCl (2×50 mL), brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe organics layer was filtered
  6. concentrationconcentrated in vacuuo
  7. customto afford material which
  8. customwas purified by column chromatography on SiO2 eluting with EtOAc in hexanes (0-50%)

出典と根拠

ORDレコード
ord-3167d46642d64bab93e6606fb0e35063
出典データセット
uspto-grants-2015_05
特許番号
US09029384B2

反応ノート

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