Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]sulfonyl]methyl]benzenepropanoate → alpha-[[[2-(Dimethylamino) ethyl]sulfonyl]methyl]benzenepropanoic acid

HRID 36748Notes

Reaction equation

HRID 36748 reaction equation
[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][S:5]([CH2:8][CH:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12]CC1C=CC=CC=1)=[O:11])(=[O:7])=[O:6]>C(O)C.[Pd]>[CH3:27][N:2]([CH3:1])[CH2:3][CH2:4][S:5]([CH2:8][CH:9]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:10]([OH:12])=[O:11])(=[O:7])=[O:6]

Participants

4

Reactant 1

HCID 15296672Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]sulfonyl]methyl]benzenepropanoate

Product 1

HCID 15780266alpha-[[[2-(Dimethylamino) ethyl]sulfonyl]methyl]benzenepropanoic acidYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound of Step 12 (150 mg, 0.4 mmol) was debenzylated in ethanol with 5 psi H2 at room temperature for 1.5 hours using 4% Pd/C catalyst. After filtering, the solvent was stripped off to give the title compound as white powder (110 mg, 70% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C14H21NO4S : C, 56.16; H, 7.07; N, 4.68. Found: C, 55.88; H, 6.99; N, 4.35.

Workup

  1. filtrationAfter filtering

Sources & evidence

ORD record
ord-f0e5a98189244934941073d0e236c8e1
Source dataset
uspto-grants-1995_05
Patent number
US05416119

Reaction notes

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