(N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester → N-(aminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester

HRID 2396788Notes

Reaction equation

HRID 2396788 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[N:5]([S:7]([NH:10]C(OCC1C=CC=CC=1)=O)(=[O:9])=[O:8])[CH3:6]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:26])[CH:4]([CH2:21][CH2:22][CH:23]([CH3:24])[CH3:25])[N:5]([S:7]([NH2:10])(=[O:8])=[O:9])[CH3:6]

Participants

4

Reactant 1

HCID 18922249(N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester

Product 1

HCID 18922252N-(aminosulfonyl)-2-(3-methylbutyl)sarcosine methyl esterYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester (20.6 g, 53.17 mmol) in 200 ml of methanol 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 3.5 hours. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo to afford 13.24 g (98.6%) of N-(aminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) as an oil.

Workup

  1. customThe catalyst was removed on a pad of CELITE®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-644c937d9d9d41558e579475107319f6
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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