HCID 86598317, compound → HCID 86598315, compound

HRID 1393372Notes

Reaction equation

HRID 1393372 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH:24]C(OC(C)(C)C)=O)=[C:15]([Cl:32])[CH:14]=1)[NH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8]>Cl.O1CCOCC1>[ClH:19].[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:12][C:13]1[CH:14]=[C:15]([Cl:32])[C:16]([O:20][CH2:21][CH2:22][CH2:23][NH2:24])=[C:17]([Cl:19])[CH:18]=1)[NH:5][C:6](=[O:11])[C:7]([F:10])([F:8])[F:9]

Participants

3

Reactant 1

HCID 86598317HCID 86598317, compound

Product 1

HCID 86598315HCID 86598315, compoundYield 200.4%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

8% Hydrochloric acid/dioxane (10 ml) was added to O-[3-(t-butoxycarbonylamino)propyl]-3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester (891 mg, 1.72 mmol) and the mixture was stirred at room temperature for 3 hrs. The solvent of the reaction mixture was distilled off under reduced pressure. To the residue was added a mixture of methanol and diisopropyl ether. The insoluble material was triturated, collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give O-(3-aminopropyl)-3,5-dichloro-N-trifluoroacetyl-L-tyrosine methyl ester hydrochloride (782 mg, 100%) as a colorless powder.

Workup

  1. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  2. additionTo the residue was added
  3. additiona mixture of methanol and diisopropyl ether
  4. customThe insoluble material was triturated
  5. filtrationcollected by filtration
  6. washwashed with diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-24136e538bed4235bc7ecba8a3f692ad
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…