Anthranilic Acid → Boc-2-Abz-OH

HRID 845377Notes

Reaction equation

HRID 845377 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])O[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].CN([CH:23]=[O:24])C>>[C:23]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:24]

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 6228DimethylformamideHCID 22251206HCID 22251206, compound

Product 1

HCID 4087778Boc-2-Abz-OH

Procedure

The pH value of a solution containing 4 g (30 mmoles) of anthranilic acid in 20 ml of DMF is adjusted to 8 by adding TEA. After adding 9 g of tertiary-butyloxy carbonate, the reaction mixture is stirred at room temperature overnight. The solvent is evaporated and the thick oily residue is dissolved in 50 ml of ethyl acetate. The organic phase is washed 3 times with 20 ml of ice-cold 0.01N sulfuric acid each, then 3 times with 20 ml of water each. The ethyl acetate solution is dried over anhydrous sodium sulfate and evaporated under reduced pressure. The thick oily residue becomes crystalline when kept in a refrigerator. The aimed product is obtained in a yield of 5.7 g (80%), m.p.: 91°-93° C.

Workup

  1. additionby adding TEA
  2. customThe solvent is evaporated
  3. dissolutionthe thick oily residue is dissolved in 50 ml of ethyl acetate
  4. washThe organic phase is washed 3 times with 20 ml of ice-cold 0.01N sulfuric acid each, then 3 times with 20 ml of water each
  5. dry with materialThe ethyl acetate solution is dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4a22f0b8a8c94f40b9fc40f2da787f13
Source dataset
uspto-grants-1988_07
Patent number
US04758552

Reaction notes

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