Potassium Carbonate → (R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxyacetic acid, methyl ester

HRID 1529

反応式

HRID 1529 の反応式
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])=[CH:10][CH:9]=1.Br[CH2:26][C:27]([O:29][CH3:30])=[O:28]>CC(C)=O>[C:20]([O:19][C:18]([NH:17][C@H:15]([CH3:16])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:9][CH:10]=1)=[O:24])([CH3:23])([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59909921(R)-2-(4-Hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester

生成物 1

HCID 86752192(R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxyacetic acid, methyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Potassium carbonate (1.95 g, 14.2 mMol) was added to a solution of (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester (2.96 g, 11.8 mMol) in acetone (50 ml) at room temperature under argon. Methyl bromoacetate (1.81 g, 11.8 mMol) was added dropwise and the reaction mixture was heated at reflux for 3 hours. The solvent was removed under reduced pressure and the residue was taken into ethyl acetate and washed with water (2×30 ml). The organic extracts were dried with sodium sulfate and the solvent evaporated in vacuo. The crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane) to give the title compound as an oil.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. washwashed with water (2×30 ml)
  5. dry with materialThe organic extracts were dried with sodium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane)

出典と根拠

ORDレコード
ord-1f90df0f79374e948d81d55edfef11d9
出典データセット
uspto-grants-1998_03
特許番号
US05726165

関連ノート

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