Hydrochloric Acid → (1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride

HRID 747767Notes

Reaction equation

HRID 747767 reaction equation
C(OC([NH:8][C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:24]=1[I:31])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O)(C)(C)C.[ClH:32]>O1CCOCC1>[Cl-:32].[CH2:14]([O:13][C:11]([CH2:10][C@@H:9]([NH3+:8])[CH2:21][O:22][C:23]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:24]=1[I:31])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11731204HCID 11731204, compound

Product 1

HCID 86760714(1R)-1-benzyloxycarbonylmethyl-2-(5-cyano-2-iodophenoxy)ethylammonium chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

11.9 g (22.1 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-(5-cyano-2-iodophenoxy)butanoate was dissolved in 120 ml of 4 N solution of hydrogen chloride in dioxane. The solution was stirred at 0° C. for one hour and then at room temperature for 2 hours. The solvent was distilled off. 50 ml of a mixed solvent of hexane/ethyl acetate in a volume ratio of 1:1 was added to the oily residue thus obtained. The precipitate formed was taken by the filtration to obtain the title compound.

Workup

  1. waitat room temperature for 2 hours
  2. distillationThe solvent was distilled off
  3. addition50 ml of a mixed solvent of hexane/ethyl acetate in a volume ratio of 1:1 was added to the oily residue
  4. customthus obtained
  5. customThe precipitate formed
  6. filtrationwas taken by the filtration

Sources & evidence

ORD record
ord-8c6bf0e3ae3047f9aa9f6dee4ac5cc65
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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