Dichloromethane → (S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-(dimethylaminomethyl) naphthalen-2-yl)acetic acid

HRID 514020ノート

反応式

HRID 514020 の反応式
[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].C1[C:33](=O)[N:32](Br)[C:30](=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH2:20][N:32]([CH3:33])[CH3:30])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 56601710(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)acetic acid

生成物 1

HCID 56601917(S)-2-tert-Butoxy-2-(1-(4-chlorophenyl)-3-(dimethylaminomethyl) naphthalen-2-yl)acetic acid収率 268.3%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

Preparation of(S)-ethyl 2-(3-(bromomethyl)-1-(4-chlorophenyl)naphthalen-2-yl)-2-tert-butoxyacetate: To a solution of (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)acetate (3K, 43 mg, 0.0105 mmol) in CCl4 (2 mL) was added NBS (24 mg, 0.13 mmol) and AIBN (cat. amount). The reaction mixture was refluxed for 5 h. After cooling to room temperature, the reaction mixture was diluted by DCM, washed with sat. NaHCO3, extracted with DCM and the organic layers were combined and dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to provide 12 mg of the desired product. 1H-MNR 400 MHz (CDCl3) δ: 8.01 (s, 1H), 7.77 (d, J=4 Hz, 1H), 7.43-7.15 (m, 7H), 5.11 (d, J=5.2 Hz, 1H), 5.06 (s, 1H), 5.00 (d, J=5.2 Hz, 1H), 4.07-4.02 (m, 2H), 1.20-1.15 (m, 3H), 0.96 (s, 9H).

後処理

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. washwashed with sat. NaHCO3
  3. extractionextracted with DCM
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-dcd9347942a44747a893a7ff4ddeb8c6
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

反応ノート

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