HCID 86679535, compound → HCID 86679536, compound

HRID 1776583Notes

Reaction equation

HRID 1776583 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:28]=[CH:27][C:26]([N:29]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[S:30]([CH3:33])(=[O:32])=[O:31])=[CH:25][C:10]=1[C:11]([O:13][CH2:14][C:15]([O:17]CC1C=CC=CC=1)=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([O:8][C:9]1[CH:28]=[CH:27][C:26]([N:29]([CH2:34][CH:35]2[CH2:36][CH2:37]2)[S:30]([CH3:33])(=[O:32])=[O:31])=[CH:25][C:10]=1[C:11]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 86679535HCID 86679535, compound

Product 1

HCID 86679536HCID 86679536, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(benzyloxy)-2-oxoethyl 2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)methylsulfonamido)benzoate (0.288 g, 0.540 mmol) and 10% w/w Pd/C (0.030 g, 0.028 mmol) in MeOH (20 ml) and EtOAc (5 ml) was hydrogenated at 20 psi for 3 hours. The catalyst was filtered off and the solvent was removed affording 2-(2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)-methylsulfonamido)benzoyloxy)-acetic acid (0.215 g, 0.485 mmol, 90% yield). This product was used without purification.

Workup

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

Sources & evidence

ORD record
ord-c12bf9593d6a47dea4d9e346561fab9c
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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