HCID 18653543, compound → HCID 18653540, compound

HRID 1728389Notes

Reaction equation

HRID 1728389 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:44])[C@H:7]([NH:25][C@H:26]([C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-])=O)[CH:36]=1)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[CH:16]=[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=[CH:13][C:12]=2[C:11]1=[O:24])([CH3:4])[CH3:3].C(O)C.O>[Pd].C(OCC)(=O)C>[CH3:1][C:2]([O:5][C:6](=[O:44])[C@H:7]([NH:25][C@H:26]([C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([NH2:41])[CH:36]=1)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[CH:16]=[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=[CH:13][C:12]=2[C:11]1=[O:24])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 18653543HCID 18653543, compoundHCID 19096565Water ethanol

Product 1

HCID 18653540HCID 18653540, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

200 mg of 4-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)-2-(R)-[[3-methyl-1-(S)-[[(3-nitrobenzyl)amino]carbonyl]butyl]amino]-butanoic acid-1,1-dimethylethyl ester, prepared as in Example 30 where the protecting group Rp, 1,1-dimethylethyl was not removed following the condensation reaction seen in Scheme 1, was added to ethanol:H2O (20:1). 10 mL of ethyl acetate was added and the mixture was stirred with heating until the solid dissolved. The mixture was cooled to RT and 20 mg of 10% palladium over activated carbon was added. The mixture was purged with nitrogen. The mixture was purged with hydrogen, and stirred under hydrogen for 3 h. The mixture was filtered and washed with ethyl acetate. The solvents were removed by evaporation and the residue was purified by reverse phase H.P.L.C. to give a white solid; 83 mg

Workup

  1. customwas not removed
  2. customthe condensation reaction
  3. temperaturewith heating until the solid
  4. dissolutiondissolved
  5. customThe mixture was purged with nitrogen
  6. customThe mixture was purged with hydrogen
  7. stirringstirred under hydrogen for 3 h
  8. filtrationThe mixture was filtered
  9. washwashed with ethyl acetate
  10. customThe solvents were removed by evaporation
  11. customthe residue was purified by reverse phase H.P.L.C
  12. customto give a white solid

Sources & evidence

ORD record
ord-3ca058632cb3498691e72d2ca6746045
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

Loading…