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

HRID 514020Notes

Reaction equation

HRID 514020 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-dcd9347942a44747a893a7ff4ddeb8c6
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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