HCID 89455858, compound → HCID 89459942, compound

HRID 1776535Notes

Reaction equation

HRID 1776535 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:16]([O:18][CH2:19][C:20]([O:22]CC1C=CC=CC=1)=[O:21])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:16]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 89455858HCID 89455858, compound

Product 1

HCID 89459942HCID 89459942, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(benzyloxy)-2-oxoethyl 3-(N-(tert-butoxycarbonyl)-methylsulfonamido)-4-methoxybenzoate (0.508 g, 1.029 mmol) in MeOH (30 m) and EtOAc (3 ml), 10% w/w Pd/C (a catalytic amount) was added, and the mixture was hydrogenated in a Parr apparatus at 20 psi for 3 hours. The catalyst was filtered off and the filtrate was evaporated to dryness affording 2-(3-(N-(tert-butoxycarbonyl)methyl-sulfonamido)-4-methoxybenzoyloxy)acetic acid (0.387 g, 0.959 mmol, 93% yield, MS/ESI+not detectable [MH]+). This product was used without any further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6c5f86c4148849ddb0d87f925925e7da
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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