Water → [2-(t-Butoxycarbonylaminomethyl)-1,4-cyclohexadienyl]acetic acid

HRID 426887Notes

Reaction equation

HRID 426887 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:8][CH:7]=[CH:6][CH2:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].[OH-].[Na+].O.[C:16]([O:20][C:21](N=[N+]=[N-])=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21]([NH:1][CH2:2][C:3]1[CH2:8][CH:7]=[CH:6][CH2:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 20564890HCID 20564890, compound

Product 1

HCID 15918136[2-(t-Butoxycarbonylaminomethyl)-1,4-cyclohexadienyl]acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8.0 g. (0.048 mole) of α-(2-aminomethyl-1,4-cyclohexadienyl)acetic acid and 3.8 g. (0.096 mole) of NaOH in 150 ml. of water was added a solution of 10.3 g. (0.072 mole) of t-butoxycarbonylazide in 80 ml. of THF and the mixture was stirred for 18 hours at room temperature. The THF was removed under reduced pressure and the residual solution was washed with ether (2×100 ml.), acidified with 6 N HC1 and extracted with ether (3×100 ml.). The combined extracts were washed with water (2×100 ml.) and a saturated NaCl solution (100 ml.), dried with Na2SO4 and evaporated to dryness.

Workup

  1. customThe THF was removed under reduced pressure
  2. washthe residual solution was washed with ether (2×100 ml.)
  3. extractionextracted with ether (3×100 ml.)
  4. washThe combined extracts were washed with water (2×100 ml.)
  5. dry with materiala saturated NaCl solution (100 ml.), dried with Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-159113b52ae64a93b2c85e001f5f79a4
Source dataset
uspto-grants-1979_10
Patent number
US04171439

Reaction notes

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