2-(Benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate → 2-(4-(Methyl-sulfonamidomethyl)benzoyloxy)acetic acid

HRID 1776560Notes

Reaction equation

HRID 1776560 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([O:13][CH2:14][C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3]>CCOC(C)=O.C(Cl)Cl.CO.[Pd]>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 866795152-(Benzyloxy)-2-oxoethyl 4-(methylsulfonamido-methyl)benzoate

Product 1

HCID 894557812-(4-(Methyl-sulfonamidomethyl)benzoyloxy)acetic acidYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 2-(benzyloxy)-2-oxoethyl 4-(methylsulfonamidomethyl)-benzoate (0.4 g, 1.060 mmol) and 10% w/w Pd/C (0.056 g, 0.053 mmol) in EtOAc and MeOH 1/1 (30 ml) was shaken under H2 atmosphere (25 psi) for 4 hours. The catalyst was removed by filtration and the filtrate was evaporated to dryness affording 2-(4-(methyl-sulfonamidomethyl)benzoyloxy)acetic acid (0.3 g, 1.044 mmol, 99% yield). The product was used without purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a1dff7de438646868507909e1f7ddb83
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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