N-(carbobenzyloxyaminosulfonyl)-2-propyl-DL-alanine methyl ester → N-aminosulfonyl-2-propyl-DL-alanine methyl ester

HRID 743449Notes

Reaction equation

HRID 743449 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([CH2:21][CH2:22][CH3:23])([CH3:20])[NH:5][S:6]([NH:9]C(OCC1C=CC=CC=1)=O)(=[O:8])=[O:7]>[Pd].CO>[CH3:1][O:2][C:3](=[O:24])[C:4]([CH2:21][CH2:22][CH3:23])([CH3:20])[NH:5][S:6]([NH2:9])(=[O:7])=[O:8]

Participants

4

Reactant 1

HCID 19424434N-(carbobenzyloxyaminosulfonyl)-2-propyl-DL-alanine methyl ester

Product 1

HCID 19424444N-aminosulfonyl-2-propyl-DL-alanine methyl esterYield 79.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(carbobenzyloxyaminosulfonyl)-2-propyl-DL-alanine methyl ester (22.35 g, 62.36 mmol), methanol (200 mL) and 10% palladium on Carbon (1.0 g) was placed on a Parr hydrogenator at 60 psi for 1.5 hours. The reaction mixture was passed through a pad of CELITE®, and the filtrate was concentrated in vacuo to afford 11.16 g (79.8%) of N-aminosulfonyl-2-propyl-DL-alanine methyl ester (Formula VII: R=CH3 ; R1 =propyl; R2 =CH3; R3 =H).

Workup

  1. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a54e83a07a394a24b675c8886c85f1c9
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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