HCID 66590858, compound → HCID 11553137, compound

HRID 1894798Notes

Reaction equation

HRID 1894798 reaction equation
[CH3:1][N:2]([CH2:12][C:13]1[CH:14]=[C:15]([C:19]2[S:23][C:22]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>CO.[Pd]>[CH3:1][N:2]([CH2:12][C:13]1[CH:14]=[C:15]([C:19]2[S:23][C:22]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 66590858HCID 66590858, compound

Product 1

HCID 11553137HCID 11553137, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 80 mg (0.20 mmol, 1 eq) of 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}thiophen-2-yl)acrylic acid (prepared as in 1 h) in 2 mL of methanol is stirred for 2 hours at room temperature in the presence of 50 mg of 10% Pd/C under a hydrogen atmosphere. The palladium is filtered off and the solvents are then evaporated off. The residue is crystallized from pentane/dichloromethane. 71 mg of 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}thiophen-2-yl)propanoic acid are obtained. Yield=89%. m.p.=67-68° C.

Workup

  1. filtrationThe palladium is filtered off
  2. customthe solvents are then evaporated off
  3. customThe residue is crystallized from pentane/dichloromethane

Sources & evidence

ORD record
ord-4999a344f7ae4163bf27dcd5c7ae3bc3
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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