Dimethylformamide → Tert-butyl[3-(5-benzyloxy-2-nitrophenoxy)benzyl]carbamate

HRID 1373219Notes

Reaction equation

HRID 1373219 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11](F)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:19]([O:23][C:24](=[O:25])[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:14]=[CH:13][C:12]=2[N+:15]([O-:17])=[O:16])[CH:29]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18369568tert-butyl N-((3-hydroxyphenyl)methyl)carbamateHCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

Product 1

HCID 21073109Tert-butyl[3-(5-benzyloxy-2-nitrophenoxy)benzyl]carbamateYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-benzyloxy-2-fluoronitrobenzene (6.43 g, 26 mmols), N-tert-butoxycarbonyl-3-hydroxybenzylamine (5.78 g, 26 mmols), potassium carbonate (3.59 g, 26 mmols) and N,N-dimethylformamide (70 ml) was stirred at 100° C. for 12 hours. The reaction mixture was cooled, then poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate, and the solvent was evaporated away to give an yellow oil of tert-butyl[3-(5-benzyloxy-2-nitrophenoxy)benzyl]carbamate (11.2 g, 95.0%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-7c980fa2674f468087cf3b0e4b38d7d5
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

Loading…