Methanol → 2-(3-Methylbutyl)-sarcosine methyl ester

HRID 743465Notes

Reaction equation

HRID 743465 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].[CH3:27]O>[Pd]>[CH3:1][O:2][C:3](=[O:26])[CH:4]([CH2:21][CH2:22][CH:23]([CH3:24])[CH3:25])[NH:5][CH3:6].[CH3:1][O:2][C:3](=[O:26])[C:4]([CH2:21][CH2:22][CH3:23])([CH3:27])[NH:5][S:7]([NH2:10])(=[O:8])=[O:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 18922249(N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester

Product 2

HCID 189222512-(3-Methylbutyl)-sarcosine methyl esterHCID 19424444N-aminosulfonyl-2-propyl-DL-alanine methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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-a90f47627b9943f6a9bef796bf83b9cd
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

Loading…