Iodoethane → Ethyl (2-chloro-5-(boc-amino)phenyl)acetate

HRID 1760029Notes

Reaction equation

HRID 1760029 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18].C([O-])([O-])=O.[K+].[K+].[CH2:26](I)[CH3:27]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH2:26][CH3:27])=[O:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 226000942-(5-{[(Tert-butoxy)carbonyl]amino}-2-chlorophenyl)acetic acid

Product 1

HCID 53922303Ethyl (2-chloro-5-(boc-amino)phenyl)acetateYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (2-chloro-5-(Boc-amino)phenyl)acetic acid (2.8 g; 9.8 mmol; from step (iv) above) in acetone (100 mL) was added K2CO3 (2.1 g, 15 mmol). EtI (70.6 g; 150 mmol) was then added whilst the reaction mixture was stirred and refluxed. The solution was concentrated, and the resultant mixture was partitioned between ether and water (1:1; 60 mL). The organic layer was separated, and the water layer was extracted once with ether (30 mL). The combined organic phase was washed with water, dried (Na2SO4), and concentrated to yield 3.0 g (98%) of the sub-title compound.

Workup

  1. temperaturerefluxed
  2. concentrationThe solution was concentrated
  3. customthe resultant mixture was partitioned between ether and water (1:1; 60 mL)
  4. customThe organic layer was separated
  5. extractionthe water layer was extracted once with ether (30 mL)
  6. washThe combined organic phase was washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6cbe150ffc6244ddb31ca0b0951da0ef
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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