Iodine → HCID 68454768, compound

HRID 2358415Notes

Reaction equation

HRID 2358415 reaction equation
[I:1]I.[C:3]([O:7][C:8](=[O:20])[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[O:18][CH3:19])([CH3:6])([CH3:5])[CH3:4]>C(Cl)Cl>[C:3]([O:7][C:8](=[O:20])[NH:9][CH2:10][C:11]1[CH:16]=[C:15]([I:1])[C:14]([NH2:17])=[CH:13][C:12]=1[O:18][CH3:19])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 807IodineHCID 68453750HCID 68453750, compound

Product 1

HCID 68454768HCID 68454768, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of iodine and AgNO2 in methylene chloride was added a solution of (4-amino-2-methoxy-benzyl)-carbamic acid tert-butyl ester (1.3 g, 5.15 mmol) in methylene chloride at 0° C., and the mixture was stirred for 30 min at 0° C. and more stirred for 30 min at ambient temperature. The reaction was quenched with Na2S2O3. The reaction solution was extracted with methylenechloride, washed with water and brine, dried over anhyd. MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (hexane/ethylacetate=2/1) to yield (4-amino-5-iodo-2-methoxy-benzyl)-carbamic acid tert-butyl ester (925 mg, 47%).

Workup

  1. stirringmore stirred for 30 min at ambient temperature
  2. customThe reaction was quenched with Na2S2O3
  3. extractionThe reaction solution was extracted with methylenechloride
  4. washwashed with water and brine
  5. customdried over anhyd
  6. filtrationMgSO4, filtered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained liquid was column-chromatographed (hexane/ethylacetate=2/1)

Sources & evidence

ORD record
ord-4ef023ab31ba43bdb6858b0403e399e7
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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