HCID 86681725, compound → HCID 86681724, compound

HRID 571316Notes

Reaction equation

HRID 571316 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:38][CH2:39][O:40][CH3:41])[CH2:9][CH2:10][N:11]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([CH2:26][C:27]([O:29]CC1C=CC=CC=1)=[O:28])[C:19]2=[O:37])[S:12]([CH3:15])(=[O:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH2:38][CH2:39][O:40][CH3:41])[CH2:9][CH2:10][N:11]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([CH2:26][C:27]([OH:29])=[O:28])[C:19]2=[O:37])[S:12]([CH3:15])(=[O:13])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86681725HCID 86681725, compound

Product 1

HCID 86681724HCID 86681724, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-(5-(N-(2-(tert-butoxycarbonyl(2-methoxyethyl)-amino)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.166 g, 0.282 mmol) and 10% w/w Pd/C (a catalytic amount) in MeOH was hydrogenated in a Parr apparatus at 30 psi for 3 hours. The catalyst was filtered off and the filtrate was evaporated to dryness affording 2-(5-(N-(2-(tert-butoxycarbonyl(2-methoxyethyl)amino)ethyl)-methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid (0.138 g, 0.276 mmol, 98% yield, MS/ESI+ 522.0 [MNa]+).

Workup

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

Sources & evidence

ORD record
ord-3613554ebf0d4ea498b69fb96fabb3e2
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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