Pyridine → Phenyl 3-fluoro-4-(3-hydroxyoxetan-3-yl)phenylcarbamate

HRID 1842919노트

반응식

HRID 1842919 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:12])[CH2:11][O:10][CH2:9]2)=[C:4]([F:13])[CH:3]=1.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>CC(C)=O>[F:13][C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][C:5]=1[C:8]1([OH:12])[CH2:9][O:10][CH2:11]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721503-(4-Amino-2-fluorophenyl)oxetan-3-ol

생성물 1

HCID 86672149Phenyl 3-fluoro-4-(3-hydroxyoxetan-3-yl)phenylcarbamate수율 59%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of 3-(4-amino-2-fluorophenyl)oxetan-3-ol (0.93 g, 5.08 mmol, 1.0 eq) in acetone (10 mL) was added pyridine (0.82 mL, 10.16 mmol, 2.0 eq) and phenyl chloroformate (0.7 mL, 5.59 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 1 h. The solvents was evaporated and the crude product was extracted with EtOAC (25 mL), diluted with water (15 mL), washed with brine (10 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. The resulting residue was washed with diethyl ether (25 mL) to get phenyl 3-fluoro-4-(3-hydroxyoxetan-3-yl)phenylcarbamate (0.892 g, 59%) as a off white solid (TLC system: 100% EtOAc, Rf: 0.55).

후처리

  1. customThe solvents was evaporated
  2. extractionthe crude product was extracted with EtOAC (25 mL)
  3. additiondiluted with water (15 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. washThe resulting residue was washed with diethyl ether (25 mL)

출처 및 근거

ORD 기록
ord-e5e2127bc1e2447b98a6caef591f6ae8
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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