(1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate → HCID 178471693, compound

HRID 1759697Notes

Reaction equation

HRID 1759697 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=S)[NH:12][C@H:13]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:17][CH:16]=1>CN(C=O)C.Cl[Hg]Cl>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C@@H:13]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:12][C:11]2[NH:10][C:3]3[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=3[N:1]=2)=[CH:16][CH:17]=1)[CH3:29]

Participants

4

Reactant 1

HCID 86594971(1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate

Product 1

HCID 178471693HCID 178471693, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

500 mg of HgCl2 is added to the amino thiourea 4-3a (530 mg, 1 mmole) in 30 ml of DMF and 3 ml of TEA, followed by agitating for 2 hours at ambient temperature, evaporating under reduced pressure and taking up in a water/NaHCO3/AcOEt mixture. The organic phase is decanted, dried and evaporated to dryness under reduced pressure. The residue is chromatographed eluting with a gradient of heptane/AcOEt (100/0→50/50). 430 mg of crude product 4-4a is obtained.

Workup

  1. customevaporating under reduced pressure
  2. customThe organic phase is decanted
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is chromatographed
  6. washeluting with a gradient of heptane/AcOEt (100/0→50/50)

Sources & evidence

ORD record
ord-8cf2a43c7ce44d55b9da5b8039facb00
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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