Hydrochloric Acid → 2-Ethylhexyl 3-{[2-amino-5-(benzyloxy)phenyl]sulfanyl}propanoate

HRID 1026269Notes

Reaction equation

HRID 1026269 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:29]([O-])=O)=[C:13]([S:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:19])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[NH2:29][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]=1[S:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580473802-Ethylhexyl 3-{[5-(benzyloxy)-2-nitrophenyl]sulfanyl}propanoate

Product 1

HCID 580474822-Ethylhexyl 3-{[2-amino-5-(benzyloxy)phenyl]sulfanyl}propanoateYield 70.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-ethylhexyl 3-{[5-(benzyloxy)-2-nitrophenyl]sulfanyl}propanoate (3.60 g) and 6M hydrochloric acid (2.69 mL) in ethanol (46 mL) was added reduced iron (4.51 g), and the mixture was heated under reflux for 3 hr. The insoluble material was removed by filtration, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a dark red liquid (2.38 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. customThe insoluble material was removed by filtration
  4. customthe solvent of the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-78b71f630caa4ebc9bc18976aacb5296
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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