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

HRID 1842919ノート

反応式

HRID 1842919 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e5e2127bc1e2447b98a6caef591f6ae8
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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