Trifluoroacetic acid → (E)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide

HRID 651781Notes

Reaction equation

HRID 651781 reaction equation
C([O:5][C:6]([C@H:8]([C@@H:18]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:19]([NH:21][N:22]1[C:26](=[O:27])[CH2:25][NH:24][C:23]1=[O:28])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([C@H:8]([C@@H:18]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:19]([NH:21][N:22]1[C:26](=[O:27])[CH2:25][NH:24][C:23]1=[O:28])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69709364(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo 1-imidazolidinyl)valeramide

Product 1

HCID 69711202(E)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramideYield 117.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.783 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in 20 ml of dichloromethane was treated with 10 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 4 hours and evaporated. Traces of trifluoroacetic acid were removed by the three-fold addition and evaporation of toluene to give 0.805 g of (E)-2(R)-[1(S)-(carboxy)-4-phenyl-3-butenyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in the form of a white solid.

Workup

  1. customevaporated
  2. customTraces of trifluoroacetic acid were removed by the three-fold addition and evaporation of toluene

Sources & evidence

ORD record
ord-502e09f53205459fba663d35a583e7d4
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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