Pyridine → Phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate

HRID 1842909노트

반응식

HRID 1842909 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:11])[CH2:10][CH2:9]2)=[C:4]([F:12])[CH:3]=1.N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>CC(C)=O>[F:12][C:4]1[CH:3]=[C:2]([NH:1][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][C:5]=1[C:8]1([OH:11])[CH2:9][CH2:10]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721471-(4-Amino-2-fluorophenyl)cyclopropanol

생성물 1

HCID 86672145Phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate수율 75%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirred solution of 1-(4-amino-2-fluorophenyl)cyclopropanol (0.7 mg, 4.19 mmol, 1.0 eq) in acetone (10 mL) was added pyridine (0.33 mL, 4.19 mmol, 1.0 eq) and phenyl chloroformate (0.5 mL, 4.19 mmol, 1.0 eq) and stirred at 0° C. to RT for 1 h. The solvent was evaporated, the residue diluted with water (10 mL×2), extracted with EtOAc (25 mL), brine (10 mL) and dried over Na2SO4 and evaporated under vacuum; the resulting residue was purified by CC using EtOAc/PE (1:4 as eluent to get phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate (0.9 g, 75%, off white solid; TLC system: EtOAc/PE (1:1), Rf: 0.6).

후처리

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water (10 mL×2)
  3. extractionextracted with EtOAc (25 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum
  6. customthe resulting residue was purified by CC

출처 및 근거

ORD 기록
ord-05b7b2c25df940ce8f87de4804a31548
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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