Phthalic Anhydride → (E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-phthalimidovaleramide

HRID 1978083Notes

Reaction equation

HRID 1978083 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:19]([NH:21][NH2:22])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]1(=O)[O:32][C:30](=[O:31])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:19]([NH:21][N:22]1[C:30](=[O:31])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]2[C:27]1=[O:32])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 69709501(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide

Product 1

HCID 86756748(E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-phthalimidovaleramideYield 44.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.0 g of (E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide and 0.41 g of phthalic anhydride in 50 ml of toluene was heated at reflux for 2 hours. The mixture was cooled and the solvent was evaporated and replaced with ethyl acetate. The ethyl acetate solution was washed with 2M aqueous hydrochloric acid, 5% aqueous sodium hydrogen carbonate and then with brine. The ethyl acetate phase was dried over anhydrous magnesium sulphate and the solvent was evaporated. The residue was trituated with diethyl ether to give 0.60 g of (E)-2(R)-[1(S)-(tertbutoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-phthalimidovaleramide in the form of a white solid.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated
  4. washThe ethyl acetate solution was washed with 2M aqueous hydrochloric acid, 5% aqueous sodium hydrogen carbonate
  5. dry with materialThe ethyl acetate phase was dried over anhydrous magnesium sulphate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e9b537f517124253aec50a3d1132ff7b
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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