Methanol → 2-(Aminosulfonylamino)pentanoic acid methyl ester

HRID 743423Notes

Reaction equation

HRID 743423 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:20]([CH3:22])C)[NH:5][S:6]([NH:9]C(OCC1C=CC=CC=1)=O)(=[O:8])=[O:7].[CH3:24]O>[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH:4]([NH:5][S:6]([NH2:9])(=[O:7])=[O:8])[CH2:20][CH2:22][CH3:24]

Participants

4

Reactant 2

HCID 887MethanolHCID 19424403N-(carbobenzyloxyaminosulfonyl)-DL-valine methyl ester

Product 1

HCID 539168252-(Aminosulfonylamino)pentanoic acid methyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of N-(carbobenzyloxyaminosulfonyl)-DL-valine methyl ester (28.5 g) in methanol (200 ml) under nitrogen was cooled to 0° C. and 1.8 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated for 2 hours. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo and purified by flash silica gel chromatography (ethyl acetate/hexane, 1:1) to afford 17.2 g (96%) of N-(aminosulfonyl)-DL-valine methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =isopropyl; R3 =H) as a solid.

Workup

  1. customThe catalyst was removed on a pad of CELITE®
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by flash silica gel chromatography (ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record
ord-6897893e253a479fba224295b6ef2999
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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