Pyridine → Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate

HRID 1842966ノート

反応式

HRID 1842966 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[CH2:9][OH:10])=[C:4]([F:14])[CH:3]=1.N1C=CC=CC=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23]>CC(C)=O>[OH:12][CH2:11][C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22](=[O:23])[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:3][C:4]=1[F:14])([CH3:13])[CH2:9][OH:10]

参加物

5

反応物 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721622-(4-Amino-2-fluorophenyl)-2-methylpropane-1,3-diol

生成物 1

HCID 86672163Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate収率 71%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred solution of 2-(4-amino-2-fluorophenyl)-2-methylpropane-1,3-diol (1.5 g, 7.53 mmol, 1.0 eq) in acetone (50 mL) was added pyridine (1.2 g, 15.18 mmol, 2.0 eq) and phenyl chloroformate (1.3 g, 8.28 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 1 h. The acetone was evaporated, and the resulting residue was diluted with EtOAc (50 mL), washed with water (100 mL), brine (20 mL) and the solvent evaporated. The crude product was purified by silica CC using EtOAc/PE (3:2) as eluent to get phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)-3-fluorophenylcarbamate (1.7 g, 71%) as a white solid (TLC system: EtOAc/PE (7:3), Rf: 0.55).

後処理

  1. customThe acetone was evaporated
  2. additionthe resulting residue was diluted with EtOAc (50 mL)
  3. washwashed with water (100 mL), brine (20 mL)
  4. customthe solvent evaporated
  5. customThe crude product was purified by silica CC

出典と根拠

ORDレコード
ord-955180924293465d9de3ba230f61d19d
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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