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

HRID 743458Notes

Reaction equation

HRID 743458 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([CH2:21][CH2:22][C:23]([CH3:26])([Cl: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:27])[CH:4]([CH2:21][CH2:22][C:23]([CH3:24])([Cl:25])[CH3:26])[N:5]([S:7]([NH2:10])(=[O:8])=[O:9])[CH3:6]

Participants

4

Reactant 1

HCID 19424411N-(carbobenzyloxyaminosulfonyl)-2-(3-methyl-3-chlorobutyl)-sarcosine methyl ester

Product 1

HCID 19424427N-(aminosulfonyl)-2-(3-methyl-3-chlorobutyl) sarcosine methyl esterYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(carbobenzyloxyaminosulfonyl)-2-(3-methyl-3-chlorobutyl)-sarcosine methyl ester (23.61 g, 55.96 mmol) in 200 ml of methanol under nitrogen was cooled to 0° C. and 1.0 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated at 50 psi for 4 hours. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo to afford 15.23 g (94.9%) of N-(aminosulfonyl)-2-(3-methyl-3-chlorobutyl)-sarcosine methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =(CH2)2C (Cl) (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-5d07c640fb9b42c18e39dea3999c9caa
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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