Ethyl chloroacetate → ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate

HRID 81188ノート

反応式

HRID 81188 の反応式
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(#N)C>[C:10]([O:9][C:8]([NH:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]1[NH:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:14])([CH3:11])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamine

生成物 1

HCID 86724541ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
55 °C

実験手順

tert-Butyl [(1S,2S)-2-aminocyclopentyl]carbamate (900 mg, 4.49 mmol) (purchased from Sigma Aldrich) was taken up in acetonitrile (13 mL). Potassium carbonate (932 mg, 6.74 mmol) and ethyl chloroacetate (0.577 mL, 5.39 mmol) were added, and the resulting mixture was heated to 55° C. overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in EtOAc, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (0-100% EtOAc/hexanes) to afford ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate.

後処理

  1. temperatureThe resulting mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (0-100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-be2625effce94f9c8aa6c25fd372ad58
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

反応ノート

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