2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester → 2-(Aminosulfonylamino)pentanoic acid methyl ester

HRID 2396764Notes

Reaction equation

HRID 2396764 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([NH:8][S:9]([NH:12]C(OCC1C=CC=CC=1)=O)(=[O:11])=[O:10])[CH2:5][CH2:6][CH3:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH:4]([NH:8][S:9]([NH2:12])(=[O:10])=[O:11])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 542695212-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester

Product 1

HCID 539168252-(Aminosulfonylamino)pentanoic acid methyl esterYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2- (N-carbobenzyloxyaminosulfonyl) aminopentanoic acid methyl ester (26.7 g) in methanol (200 ml) under nitrogen was cooled to 0° C. and 1.5 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 (4-6% methanol in methylene chloride) to afford 11.0 g (62%) of 2-(aminosulfonylamino)pentanoic acid methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 63°-64° C.

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 (4-6% methanol in methylene chloride)

Sources & evidence

ORD record
ord-9009730ba5cd4b22aa9accbfa523e32d
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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