Methanol → 2-(Aminosulfonylamino)pentanoic acid methyl ester

HRID 1289622Notes

Reaction equation

HRID 1289622 reaction equation
C([NH:11][S:12]([NH:15][CH:16]([CH2:20][CH2:21][CH3:22])[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])(OCC1C=CC=CC=1)=O.[CH3:23]O>[Pd]>[CH3:23][O:19][C:17](=[O:18])[CH:16]([NH:15][S:12]([NH2:11])(=[O:14])=[O:13])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 887MethanolHCID 189222562-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid

Product 1

HCID 539168252-(Aminosulfonylamino)pentanoic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid (46.7 g), methanol (350 mL) and 10% palladium on carbon (3.0 g) was hydrogenated at 55 psi for about 2 hours. The catalyst was removed by filtration through CELITE®, the solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 50% ethyl acetate/hexane to afford 25.6 g (90%) of 2-(aminosulfonylamino)pentanoic acid methyl ester (Formula V: R=CH3 ; R1 =propyl; R2 =H; R3 =H), m.p. 63°-64° C.

Workup

  1. customThe catalyst was removed by filtration through CELITE®
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ff6a248b0c284366b26da0c5aff681d4
Source dataset
uspto-grants-1998_05
Patent number
US05750546

Reaction notes

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