HCID 18461276, compound → HCID 77844759, compound

HRID 2303809Notes

Reaction equation

HRID 2303809 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:43]=[CH:42][C:12]([O:13][CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)=[CH:20][C:19]=3[N:33]([CH3:41])C(=O)OC(C)(C)C)=O)=[CH:11][CH:10]=2)[S:3]1>FC(F)(F)C(O)=O>[CH3:41][N:33]1[C:19]2[CH:20]=[C:21]([O:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[CH:22]=[CH:23][C:18]=2[N:17]=[C:15]1[CH2:14][O:13][C:12]1[CH:42]=[CH:43][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 18461276HCID 18461276, compound

Product 1

HCID 77844759HCID 77844759, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of t-butyl N-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-(4-methoxyphenoxy)phenyl}-N-methylcarbamate (3.28 g) in trifluoroacetic acid (50 ml) was stirred at 65° C. for 8 hours and allowed to stand at ambient temperature for 1 night. The reaction mixture was concentrated and to the residue was added water and neutralized with aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate and then evaporated. On addition of ether/ethyl acetate=1/1 to the residue crystals were formed and isolated by filtration to give the title compound (1.91 g).

Workup

  1. waitto stand at ambient temperature for 1 night
  2. concentrationThe reaction mixture was concentrated and to the residue
  3. additionwas added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. additionOn addition of ether/ethyl acetate=1/1 to the residue crystals
  9. customwere formed
  10. customisolated by filtration

Sources & evidence

ORD record
ord-db89203a50d847d086ca7eb66941904a
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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