Carbon Dioxide → 2-(tert-Butoxycarbonylamino)-3-fluoro-benzoic acid

HRID 558978Notes

Reaction equation

HRID 558978 reaction equation
C([Li])(C)(C)C.CCCCC.[C:11]([O:15][C:16](=[O:25])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24])([CH3:14])([CH3:13])[CH3:12].[C:26](=[O:28])=[O:27]>O.C1COCC1>[C:11]([O:15][C:16]([NH:17][C:18]1[C:19]([F:24])=[CH:20][CH:21]=[CH:22][C:23]=1[C:26]([OH:28])=[O:27])=[O:25])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8003PentaneHCID 4935500Tert-butyl 2-fluorophenylcarbamateHCID 178418306HCID 178418306, compound

Product 1

HCID 112882942-(tert-Butoxycarbonylamino)-3-fluoro-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyllithium in pentane (1.7M, 34 ml, 58 mmol) was added with caution to a solution of (2-fluoro-phenyl)-carbamic acid tert-butyl ester whilst cooling to less than −50° C. The mixture was maintained at this temperature, stirred for 3 h then poured onto a slurry of THF and dry ice. The mixture was allowed to warm to room temperature, diluted with water and evaporated in vacuo. The residue was taken up in water and washed with diethyl ether. A solution of 0.3M potassium hydrogen sulphate was added until pH6 and extracted with chloroform. The chloroform extracts were combined, washed with brine, dried and reduced to give a white solid; yield 2.7 g, 37%.

Workup

  1. temperaturewhilst cooling to less than −50° C
  2. temperatureThe mixture was maintained at this temperature
  3. customevaporated in vacuo
  4. washwashed with diethyl ether
  5. additionA solution of 0.3M potassium hydrogen sulphate was added until pH6
  6. extractionextracted with chloroform
  7. washwashed with brine
  8. customdried
  9. customto give a white solid

Sources & evidence

ORD record
ord-a7eaf5f8abee4769ac257656d83d7351
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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