Hydrochloric Acid → HCID 86626089, compound

HRID 390628Notes

Reaction equation

HRID 390628 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH2:17]([O:21][C:22]1[CH:27]=[C:26](/[CH:28]=[C:29](\[CH3:35])/[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:25]=[CH:24][C:23]=1[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][NH:43][CH3:44])[CH:37]=1)[CH2:18][CH2:19][CH3:20].C(N(CC)CC)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([CH2:44][NH:43][CH2:42][C:38]1[CH:37]=[C:36]([C:23]2[CH:24]=[CH:25][C:26](/[CH:28]=[C:29](\[CH3:35])/[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][C:22]=2[O:21][CH2:17][CH2:18][CH2:19][CH3:20])[CH:41]=[CH:40][CH:39]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86626087HCID 86626087, compound

Product 1

HCID 86626089HCID 86626089, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

142 μL of benzoyl chloride (1.2 mmol) are added to a solution of 0.36 g (0.6 mmol) of ethyl (E)-3-(2-butoxy-3′-methylaminomethylbiphenyl-4-yl)-2-methylacrylate trifluoroacetate, 6.5 mL of dichloromethane, 257 μL (1.84 mmol) of triethylamine and 7 mg (10 mol %) of 4-dimethylaminopyridine. The reaction medium is stirred at room temperature for 18 hours and then treated with 1 N hydrochloric acid solution and washed with water. The organic phase is dried over magnesium sulfate, filtered and evaporated. The crude residue obtained is purified by chromatography on a column of silica eluted with an 85/15 and then 70/30 heptane/ethyl acetate mixture. 270 mg (91%) of ethyl (E)-3-{3′-[(benzoylmethylamino)methyl]-2-butoxybiphenyl-4-yl}-2-methylacrylate are obtained in the form of a yellow oil.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with an 85/15

Sources & evidence

ORD record
ord-98547934affd4ff687d13bab7c1fe9e9
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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