Potassium Iodide → HCID 19070827, compound

HRID 1955602Notes

Reaction equation

HRID 1955602 reaction equation
NC1C=C(O)C=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[C:24]([O:28][C:29]([NH:31][C:32]1[CH:33]=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=1)=[O:30])([CH3:27])([CH3:26])[CH3:25].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O>[C:24]([O:28][C:29]([NH:31][C:32]1[CH:33]=[C:34]([O:38][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:35]=[CH:36][CH:37]=1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 90495Di-tert-butyl dicarbonateHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

Product 1

HCID 19070827HCID 19070827, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-aminophenol (2.18 g, 20 mmol) in tetrahydrofuran (10 ml) is added di-tert-butyl dicarbonate (4.578 g, 21 mmol) and the mixture is stirred for 15 hr at room temperature. To the residue obtained by concentrating the reaction mixture is purified by chromatography on silica gel (hexane/ethyl acetate (5:1)). To a solution of the resultant oily residue of 3-(N-tert-butyloxycarbonylamino)phenol in dimethylformamide are added ethyl 2-bromoacetate (2.44 ml, 22 mmol), potassium iodide (183 mg, 1.1 mmol) and potassium carbonate (3.04 g, 22 mmol) and the mixture is stirred for 15 hr at room temperature. The reaction mixture is concentrated under reduced pressure and the concentrate is partitioned between a mixture of ethyl acetate and water. The organic layer is dried over magnesium sulfate and concentrated under reduced pressure. The resultant crude product is purified by chromatography on silica gel (toluene/ethyl acetate (9:1)) to give the titled compound as colorless oil.

Workup

  1. customTo the residue obtained
  2. concentrationby concentrating the reaction mixture
  3. customis purified by chromatography on silica gel (hexane/ethyl acetate (5:1))
  4. stirringthe mixture is stirred for 15 hr at room temperature
  5. concentrationThe reaction mixture is concentrated under reduced pressure
  6. customthe concentrate is partitioned between a mixture of ethyl acetate and water
  7. dry with materialThe organic layer is dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant crude product is purified by chromatography on silica gel (toluene/ethyl acetate (9:1))

Sources & evidence

ORD record
ord-f8e574e60a3f4d3182db096135a5b853
Source dataset
uspto-grants-1998_07
Patent number
US05776929

Reaction notes

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