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

HRID 1360352노트

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HRID 1360352 반응식
[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]

참가 물질

9

반응물 5

HCID 313Hydrochloric Acid2회HCID 887MethanolHCID 14798Sodium HydroxideHCID 83311Ethyl 3-(cyanomethyl)benzoate2회HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 6386tert-Butanol용매

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온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7bed46fc312b4cceb6d1cd3f0f9453ef
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879853B2

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