tert-butyl N-(2-hydroxyethyl)carbamate → HCID 57602495, compound

HRID 1787905Notes

Reaction equation

HRID 1787905 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].F[C:19]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1.ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:26]1[CH:27]=[C:28]([F:30])[CH:29]=[CH:19][C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 2737170Benzoic acid, 2,4-difluoro-, ethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 57602495HCID 57602495, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(tert-butoxycarbonylamino)ethanol (4.34 g, 26.9 mmol) in THF (16 mL) at 0° C. under N2, was added potassium tert-butoxide (K+−OtBu, 26.9 mL, 26.9 mmol, 1.0 M in THF). The reaction mixture was stirred for 20 min at 0° C. during which time a thick slurry formed. The anion solution was then poured into a solution of ethyl 2,4-di-fluorobenzoate (5.00 g, 26.9 mmol) in THF (16 mL) which had been cooled to −65° C. The reaction mixture was allowed to slowly warm to room temperature and was stirred for 18 h. The mixture was diluted with dichloromethane and washed with water. The water layer was extracted with additional dichloromethane and the dichloromethane layers combined and washed with brine, dried, and concentrated in vacuo to give a yellow oil. Purification on silica gel, eluting with a gradient of 4:1 to 3:1 hexane:EtOAc, yielded 3.82 g (43.5%) of the ether as a colorless oil.

Workup

  1. customformed
  2. temperaturehad been cooled to −65° C
  3. temperatureto slowly warm to room temperature
  4. stirringwas stirred for 18 h
  5. washwashed with water
  6. extractionThe water layer was extracted with additional dichloromethane
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil
  11. customPurification on silica gel
  12. washeluting with a gradient of 4:1 to 3:1 hexane
  13. customEtOAc, yielded 3.82 g (43.5%) of the ether as a colorless oil

Sources & evidence

ORD record
ord-2ed4140d900344f8850149539ced1594
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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