HCID 67494711, compound → HCID 67494912, compound

HRID 1620384Notes

Reaction equation

HRID 1620384 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][CH2:28][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>C(OCC)(=O)C.O1CCOCC1.C(O)(=O)C.[Pd]>[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][CH2:28][CH2:27][CH2:26]2)[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

6

Reactant 1

HCID 67494711HCID 67494711, compound

Product 1

HCID 67494912HCID 67494912, compoundYield 100.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4.9 g (11 mmol) of methyl(S)-3-(4-benzyloxybenzenesulfonylamino)-2-piperidin-1-yl-propanoate (prepared as described in 1.5) in 80 ml of ethyl acetate, 30 ml of dioxane and 0.5 ml of glacial acetic acid is degassed under nitrogen for 15 min and then a suspension of 490 mg (10% by weight) of palladium on carbon at 10% in 3 ml of dioxane is added. The reaction medium is then placed under a hydrogen atmosphere and stirred at ambient temperature for 5 h. After filtration through celite, the filtrate is concentrated under vacuum. The residue is taken up in ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. 3.8 g (97%) of methyl (S)-3-(4-hydroxybenzenesulfonylamino)-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.

Workup

  1. additionis added
  2. filtrationAfter filtration through celite
  3. concentrationthe filtrate is concentrated under vacuum
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45228442ef7647c1bf01a98d25e25abe
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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