Nitric Acid → Fmoc-Phe-N-Me-Val-Tyr(3-NO2)-NH2

HRID 1356732Notes

Reaction equation

HRID 1356732 reaction equation
[NH:1]([C:33]([O:35][CH2:36][CH:37]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[C@H:2]([C:10]([N:12]([CH3:32])[C@H:13]([C:17]([NH:19][C@H:20]([C:29]([NH2:31])=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[N+:51]([O-])([OH:53])=[O:52]>C(Cl)Cl.C(O)(=O)C>[NH:1]([C:33]([O:35][CH2:36][CH:37]1[C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[C:49]1=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:34])[C@H:2]([C:10]([N:12]([CH3:32])[C@H:13]([C:17]([NH:19][C@H:20]([C:29]([NH2:31])=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([N+:51]([O-:53])=[O:52])[CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 131723960Fmoc-Phe-N-Me-Val-Tyr-NH2

Product 1

HCID 131723961Fmoc-Phe-N-Me-Val-Tyr(3-NO2)-NH2Yield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Fmoc-Phe-N-Me-Val-Tyr-NH2 (230 mg, 0.340 mmol) in methylene chloride (1 ml) and acetic acid (1 ml), fuming nitric acid (0.03 ml) was added under cooling with ice, followed by stirring at room temperature for 1 hour. The reaction mixture was mixed with water and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=2:1) to give the titled compound (204 mg, 83%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-1134d9cdfae84201b66fa5d631870b7d
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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