Methanol → 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester

HRID 2396780Notes

Reaction equation

HRID 2396780 reaction equation
[C:1]([NH:11][S:12]([NH:15][CH:16]([CH2:20][CH2:21][CH3:22])[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23]O>[Pd]>[CH3:23][O:18][C:17](=[O:19])[CH:16]([NH:15][S:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])(=[O:14])=[O:13])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

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

Product 1

HCID 542695212-(N-carbobenzyloxyaminosulfonyl)aminopentanoic 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 XIV: R=CH3 ; R1 =H; R2 =propyl; 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-9ada986ad5104a96ad941e38bed3de71
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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