Phenyl chloroformate → Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate

HRID 1842972ノート

反応式

HRID 1842972 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])=[CH:4][CH:3]=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]>C([O-])(O)=O.[Na+].O.C1COCC1>[OH:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:15](=[O:16])[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)([CH3:13])[CH2:11][OH:12]

参加物

6

反応物 2

HCID 15891Phenyl chloroformateHCID 594100922-(4-Aminophenyl)-2-methylpropane-1,3-diol

生成物 1

HCID 86672164Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate収率 66.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-(4-aminophenyl)-2-methylpropane-1,3-diol (1 g, 5.52 mmol, 1.0 eq) in sat. aq. NaHCO3 (4 mL), water (2 mL) and THF (4 mL) was added phenyl chloroformate (0.76 mL, 6.08 mmol, 1.1 eq) at 0° C. and the mixture was stirred at 0° C. for 0.5 h. The mixture was diluted with water (10 mL) and extracted with EtOAc (2×30 mL). The combined organic layer was washed with brine (10 mL) and the solvent evaporated. The crude product was purified by CC using chloroform/MeOH (95:5) as eluent to get phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate (1.1 g, 60%) as a white solid (TLC system: chloroform—MeOH; 9:1; Rf: 0.4).

後処理

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic layer was washed with brine (10 mL)
  3. customthe solvent evaporated
  4. customThe crude product was purified by CC

出典と根拠

ORDレコード
ord-a065c8adcd224eadbafb55228de82054
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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