HCID 86679520, compound → HCID 86679521, compound

HRID 1776565Notes

Reaction equation

HRID 1776565 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]([C:10]([O:12][CH2:13][C:14]([O:16]CC3C=CC=CC=3)=[O:15])=[O:11])=[CH:8][C:7]=2[O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:3][CH2:2]1>CO.CCOC(C)=O.[Pd]>[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]([C:10]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[O:11])=[CH:8][C:7]=2[O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 86679520HCID 86679520, compound

Product 1

HCID 86679521HCID 86679521, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-(methylsulfonyloxy)benzoate (0.238 g, 0.548 mmol) and 10% w/w Pd/C (0.030 g, 0.028 mmol) in MeOH (17 ml) and EtOAc (3 ml) was hydrogenated at 20 psi for 2 hours. The catalyst was filtered off, and the solvent was removed under vacuum affording 2-(4-(cyclopropylmethoxy)-3-(methylsulfonyloxy)benzoyloxy)acetic acid (0.178 g, 0.517 mmol, 94% yield, MS/ESI+ 344.9 [MH]+). The product was used without any further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-56b1769ee74c46089774a574690e2d11
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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