Water → [4-(2-Acetyl-3-benzyloxyphenoxy)-butyl]-carbamic Acid Tert-butyl Ester

HRID 660615Notes

Reaction equation

HRID 660615 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=1[C:16](=[O:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:31])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29]I)([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:19]([O:23][C:24](=[O:31])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]=1[C:16](=[O:18])[CH3:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27751871-[2-(Benzyloxy)-6-hydroxyphenyl]ethan-1-oneHCID 53439149tert-Butyl (4-iodobutyl)carbamate

Product 1

HCID 68840692[4-(2-Acetyl-3-benzyloxyphenoxy)-butyl]-carbamic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-benzyloxy-6-hydroxyphenyl)-ethanone (100 mg, 0.41 mmol) and (4-iodobutyl)-carbamic acid tert-butyl ester (Example 123, step A) (150 mg, 0.5 mmol) in DMF (5 mL) is added K2CO3 (113 mg, 0.82 mmol) and the mixture is stirred at RT for 18 h. Water is added and the mixture is extracted with EtOAc. The organic phase is washed with water and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using hexane/EtOAc (10:1) as eluent to give the title compound as a white solid.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic phase is washed with water and brine
  3. dry with materialthen is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-a47b976137d444a5aa118926e8aec871
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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