HCID 14365061, compound → HCID 90308267, compound

HRID 2278813Notes

Reaction equation

HRID 2278813 reaction equation
[NH:1]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[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]>[NH:1]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[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]([NH2:24])=[CH:20][CH:19]=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 14365061HCID 14365061, compound

Product 1

HCID 90308267HCID 90308267, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1.6 g (3.00 mmol) Boc-D-Phe(4-NO2)-Phe(4-NO2)—OMe (4a) was dissolved in 150 ml of 90% acetic acid. Then, 160 mg Pd—C was added, purged 3× and hydrogenated overnight at RT. After filtration of the suspension, the solvent was removed in vacuo. The residue was taken up in sat. NaHCO3 soln./EtOAc and the organic phase was washed 3× with sat. NaHCO3 soln. and 2× with sat. NaCl soln. The organic phase was dried with MgSO4, followed by filtration and removal of the solvent in vacuo.

Workup

  1. custompurged 3× and hydrogenated overnight at RT
  2. filtrationAfter filtration of the suspension
  3. customthe solvent was removed in vacuo
  4. wash/EtOAc and the organic phase was washed 3× with sat. NaHCO3 soln
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfollowed by filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-75b909f15d314aca87a4d53784b6ff7d
Source dataset
uspto-grants-2015_09
Patent number
US09133194B2

Reaction notes

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