Dimethylformamide → 3-Pyridylthio-2-phenylbenzoic acid tert-butyl ester

HRID 2121211노트

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HRID 2121211 반응식
[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([N+]([O-])=O)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].Cl.COC(=O)[C@H:27]([CH2:44][CH2:45][S:46]C)NC(=O)C1C=CC(N)=CC=1C1C=CC=CC=1.[CH3:49][N:50]([CH:52]=O)C>C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:46][C:45]2[CH:49]=[N:50][CH:52]=[CH:27][CH:44]=2)[C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 113923934-Nitro-2-phenylbenzoic acid tert-butyl esterHCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride2회

생성물 1

HCID 538048533-Pyridylthio-2-phenylbenzoic acid tert-butyl ester수율 51%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

To a mixture in DMF (2 mL) of 4-nitro-2-phenylbenzoic acid tert-butyl ester (403 mg, 1.35 mmol), prepared by esterification of 4-nitro-2-phenylbenzoic acid (compound 8, step B), and 3-thiopyridine sodium salt (224 mg, 1.68 mmol), prepared as in 232C, was stirred at 100° C. for 60 hours. The reaction mixture was cooled to ambient temperature and diluted with saturated aqueous sodium bicarbonate. The mixture was extracted with ether (3×). The combined ether extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to give a brown oil. Chromatography on silica gel (10% ethyl acetate-hexanes) gave 3-pyridylthio-2-phenylbenzoic acid tert-butyl ester as a colorless oil (248 mg, 51%).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted with ether (3×)
  3. dry with materialThe combined ether extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil

출처 및 근거

ORD 기록
ord-1c68836943cb46079fe6d6056f32147f
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693123B2

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