Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}-2-propenoate → Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]-phenyl}propanoate

HRID 896488Notes

Reaction equation

HRID 896488 reaction equation
[C:1]([C:9]1[CH:33]=[CH:32][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O1CCOCC1.[Pd]>[C:1]([C:9]1[CH:33]=[CH:32][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69796345Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}-2-propenoate

Product 1

HCID 22351065Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]-phenyl}propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21966525Dioxane MethanolSolvent

Procedure

The compound obtained in Example 31 is dissolved in a methanol/dioxane mixture and then a catalytic amount of palladium-on-carbon is added. The reaction is stirred at ambient temperature under a hydrogen atmosphere for from 6 to 15 hours. The carbon is then filtered off and the solvents are removed by evaporation in vacuo. The resulting residue is recrystallised from methanol to yield the title product.

Workup

  1. filtrationThe carbon is then filtered off
  2. customthe solvents are removed by evaporation in vacuo
  3. customThe resulting residue is recrystallised from methanol

Sources & evidence

ORD record
ord-ce86838c730e4a03a3bb82dcb1759948
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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