HCID 53981280, compound → HCID 20482537, compound

HRID 648318Notes

Reaction equation

HRID 648318 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([O:25][CH:26]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[CH:21][CH:20]=1.[H][H]>[Pd].O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:24])=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 53981280HCID 53981280, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20482537HCID 20482537, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4 g. 2-(ethoxycarbonyl)vinyl 4-(16-bromohexadecylamino)benzoate and 400 mg. 10% palladium-on-carbon in 100 ml. tetrahydrofuran is hydrogenated at 50 psi until hydrogen uptake stops. The catalyst is filtered, the solution is evaporated, and the residue is crystallized from acetonitrile to yield 2-(ethoxycarbonyl)ethyl 4-(16-bromohexadecylamino)benzoate.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solution is evaporated
  3. customthe residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-3039332e297b453fa053cdfc52048e65
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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