Benzoyl chloride → 3-[2-(Benzoylamino-methyl)4-hydroxy-phenyl]propionic acid tert-butyl ester

HRID 1181047ノート

反応式

HRID 1181047 の反応式
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH2:17])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 17984622Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate

生成物 1

HCID 589795203-[2-(Benzoylamino-methyl)4-hydroxy-phenyl]propionic acid tert-butyl ester収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A slurry of 3-(2-aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester (0.36 g, 1.43 mmol) in CH2Cl2 (10 mL) was cooled in an ice-water bath and treated with triethyl amine (0.40 mL, 0.28 mmol) then dropwise with benzoyl chloride (0.18 mL, 1.55 mmol). The resulting solution was stirred 30 min, and the cooling bath was removed. After 30 min, the solution was concentrated, and the residue was partitioned between EtOAc (50 mL) and 1N HCl (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), and concentrated to a solid. The crude mixture was purified by radial chromatography (hexanes:EtOAc 3:1 to 2:1) to give the title compound as a white solid (325 mg, 64%): 1H NMR (400 MHz, CDCl3) 1.26 (s, 9H), 2.54 (t, J=7.1 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 4.55 (d, J=2H), 6.68 (dd, J=8.3, 2.4 Hz, 1H), 6.86 (d, J=2.9 Hz, 1H), 6.96 (d, J=8.3 Hz, 1H), 7.25-7.29 (m, 2H), 7.34-7.37 (m, 1H), 7.49 (br s, 1H), 7.16-7.79 (m, 2H); MS (ES) m/z 356.2 (M+H).

後処理

  1. customthe cooling bath was removed
  2. waitAfter 30 min
  3. concentrationthe solution was concentrated
  4. customthe residue was partitioned between EtOAc (50 mL) and 1N HCl (10 mL)
  5. washThe organic layer was washed with brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to a solid
  8. customThe crude mixture was purified by radial chromatography (hexanes:EtOAc 3:1 to 2:1)

出典と根拠

ORDレコード
ord-ac6b2ac2f6264921b01f6f22b88755ca
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

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