Hydrochloric Acid → 3-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

HRID 1360352ノート

反応式

HRID 1360352 の反応式
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9]CC)=[O:8])#[N:2].Cl.[H][H].[OH-:18].[Na+].[CH3:20][OH:21]>C(O)C.[Pd].C(O)(C)(C)C>[C:4]([O:18][C:20]([NH:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([OH:9])=[O:8])=[O:21])([CH3:5])([CH3:14])[CH3:3]

参加物

9

反応物 5

HCID 313Hydrochloric Acid2 回HCID 887MethanolHCID 14798Sodium HydroxideHCID 83311Ethyl 3-(cyanomethyl)benzoate2 回HCID 178418361HCID 178418361、化合物

生成物 1

HCID 233606753-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
40 °C

実験手順

Ethyl 3-cyanomethyl-benzoate (compound E5) (7.15 g, 41 mmol) is dissolved in ethanol (200 mL) and concentrated hydrochloric acid (5 mL), Pd/C (2 g) is added and the mixture is hydrogenated at 3 bar hydrogen pressure for 24 h. Afterwards, the mixture is filtered, evaporated and the residue is treated with methanol (120 mL) and aqueous 2N NaOH (50 mL, 0.1 mol) and heated 6 h at 40° C., filtered and the filtrate treated with aqueous 2N hydrochloric acid (32 mL, 64 mmol). Boc-anhydride (Boc2O) (9.81 g, 45 mmol) and tertbutanol are added and stirred for 16 h at ambient temperature. The mixture is evaporated, the residue is extracted with dichloromethane/ethyl acetate (1:1, 3×30 mL) and water. After evaporation the organic phase is purified by flash chromatography.

後処理

  1. filtrationAfterwards, the mixture is filtered
  2. customevaporated
  3. filtrationfiltered
  4. customThe mixture is evaporated
  5. extractionthe residue is extracted with dichloromethane/ethyl acetate (1:1, 3×30 mL) and water
  6. customAfter evaporation the organic phase
  7. customis purified by flash chromatography

出典と根拠

ORDレコード
ord-7bed46fc312b4cceb6d1cd3f0f9453ef
出典データセット
uspto-grants-2011_02
特許番号
US07879853B2

反応ノート

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