HCID 131733471, compound → HCID 131733472, compound

HRID 2278811Notes

Reaction equation

HRID 2278811 reaction equation
[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:27]([O:29][CH3:30])=[O:28])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1>C(O)(=O)C.[Pd]>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:27]([O:29][CH3:30])=[O:28])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=1)=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 131733471HCID 131733471, compound

Product 1

HCID 131733472HCID 131733472, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.0 g (1.47 mmol) Chas-D-Phe(4-NO2)-Phe(4-NO2)—OMe was dissolved in 200 ml of 90% acetic acid, mixed with 101 mg of Pd—C, purged 3× and hydrogenated overnight with hydrogen. The catalyst was filtered off and the solvent removed in vacuo. The red, viscous oil was dissolved in 8 ml of 25% solvent B, filtered through a 0.2 μm filter and purified by prep. HPLC (start at 10% B). Fractions containing the product were combined, the solvent removed in vacuo, the residue dissolved in 40% t-butanol/water and lyophilized.

Workup

  1. custompurged 3× and hydrogenated overnight with hydrogen
  2. filtrationThe catalyst was filtered off
  3. customthe solvent removed in vacuo
  4. dissolutionThe red, viscous oil was dissolved in 8 ml of 25% solvent B
  5. filtrationfiltered through a 0.2 μm
  6. filtrationfilter
  7. custompurified by prep
  8. additionFractions containing the product
  9. customthe solvent removed in vacuo
  10. dissolutionthe residue dissolved in 40% t-butanol/water

Sources & evidence

ORD record
ord-95ca61820dfe47dc97f5d920a664a88e
Source dataset
uspto-grants-2015_09
Patent number
US09133194B2

Reaction notes

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