Hydrochloric Acid → HCID 11349656, compound

HRID 1595059Notes

Reaction equation

HRID 1595059 reaction equation
C[NH:2][C@H:3]([C:12]([O-:14])=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.N1C=CC=C[CH:16]=1.C[Si](Cl)(C)C.[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[S:36](Cl)(=[O:38])=[O:37].Cl>C(Cl)Cl>[CH3:16][O:14][C:12](=[O:13])[C@@H:3]([NH:2][S:36]([C:27]1[CH:28]=[CH:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=1)(=[O:38])=[O:37])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 71252-Naphthalenesulfonyl chlorideHCID 86757348HCID 86757348, compound

Product 1

HCID 11349656HCID 11349656, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyltyrosinate(1 g, 4.32 mmol) was suspended in 5 ml of methylene chloride, pyridine(1.4 ml, 17.28 mmol) was added thereto, and the reaction mixture was allowed to stand until the mixture became thoroughly transparent. After the reaction solution became transparent, trimethylsilylchloride(1.1 ml, 8.64 mmol) was slowly added thereto at room temperature. After 1 hour, 2-naphthalenesulfonylchloride(1.08 g, 4.75 mmol) was added and the resulting mixture was stirred for 24 hours. To this mixture was added 3N HCl solution, which was then stirred for about 2 hours. The organic layer was separated, the aqueous layer was extracted with methylene chloride, and the organic layers were combined. The combined organic layer was dried over Na2SO4 and the organic solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from toluene to give 1.29 g(Yield 79%) of the title compound as a white solid.

Workup

  1. customat room temperature
  2. stirringwas then stirred for about 2 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. customthe organic solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was recrystallized from toluene

Sources & evidence

ORD record
ord-740af75904f94a458c9b4539d211763a
Source dataset
uspto-grants-2001_09
Patent number
US06284912B1

Reaction notes

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