HCID 67494688, compound → HCID 67494612, compound

HRID 1620389Notes

Reaction equation

HRID 1620389 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][C@H:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO.O1CCOCC1>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH2:19][C@H:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 67494688HCID 67494688, compound

Product 1

HCID 67494612HCID 67494612, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

0.4 g of palladium on carbon at 10% is added to a solution of 4 g (9.2 mmol) of methyl(S)-3-(4-benzyloxybenzenesulfonylamino)-2-morpholin-4-ylpropanoate (prepared as described in example 7.3) in 200 ml of methanol and 20 ml of dioxane degassed beforehand with nitrogen. The reaction mixture is stirred for one hour at ambient temperature under atmospheric hydrogen pressure. After filtration through celite and concentration of the filtrate under vacuum, the residue obtained is purified by chromatography on silica gel, elution being carried out with a 60/40 ethyl acetate/heptane mixture. 2.6 g (81%) of methyl(S)-3-(4-hydroxybenzenesulfonylamino)-2-morpholin-4-ylpropanoate are obtained in the form of a white solid.

Workup

  1. filtrationAfter filtration through celite and concentration of the filtrate under vacuum
  2. customthe residue obtained
  3. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-074ae4fd155e4216b5527f69159c9426
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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