Sodium Iodide → HCID 68538779, compound

HRID 2389318Notes

Reaction equation

HRID 2389318 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]=1[NH:16][C:17](=[O:19])[CH3:18].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:17]([NH:16][C:3]1[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 68538324HCID 68538324, compound

Product 1

HCID 68538779HCID 68538779, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of N-[2-amino-6-(benzyloxy)phenyl]acetamide (2.95 g) and ethyl bromoacetate (2.11 g) in DMF (29.5 mL) were added sodium iodide (1.73 g) and K2CO3 (1.91 g) at ambient temperature. The mixture was stirred at 80° C. for 6 hours. After cooling, the reaction mixture was added water (50 mL). The formed precipitate was collected by filteration and washed with water and recrystallized from solvent (EtOAc and n-hexane) to give ethyl N-[2-acetamido-3-(benzyloxy)phenyl]glycinate (2.86 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. customThe formed precipitate was collected by filteration
  3. washwashed with water
  4. customrecrystallized from solvent (EtOAc and n-hexane)

Sources & evidence

ORD record
ord-f2ea4840a7ff4ef4966d51d9f4f7d93d
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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