HCID 19017448, compound → HCID 18653509, compound

HRID 1728393Notes

Reaction equation

HRID 1728393 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:45])[CH:7]([NH:29][CH:30]([C:35]([NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20]CC3C=CC=CC=3)[CH:16]=2)[C:11]1=[O:28])([CH3:4])[CH3:3].[H][H]>[Pd].C(O)C>[CH3:1][C:2]([O:5][C:6](=[O:45])[C@H:7]([NH:29][C@H:30]([C:35]([NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=2)[C:11]1=[O:28])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 19017448HCID 19017448, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18653509HCID 18653509, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

100 mg of 2-[1-(benzylamino)carbonyl-3-methyl-butylamino]-4-(5-benzyloxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butanoic acid-1,1-dimethylethyl ester, prepared as in Example 76 where the protecting group Rp, 1,1-dimethylethyl, was not removed following the condensation reaction seen in Scheme 2, was added to 10 mg of 10% Palladium on carbon in 2.5 mL absolute ethanol under 1 atmosphere of hydrogen. The mixture was stirred for 15 h and filtered through celite. The solvent was removed by evaporation and the residue was w ashed with hexane. The solvent was removed by evaporation yielding 66 mg of a white solid

Workup

  1. customwas not removed
  2. customthe condensation reaction
  3. filtrationfiltered through celite
  4. customThe solvent was removed by evaporation
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-27939c20a8f04075952dac3b7ee5c8dc
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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