4-Nitrophenol → N-((Phenylmethoxy)carbonyl)glycine 4-nitrophenyl ester

HRID 1283232

Reaction equation

HRID 1283232 reaction equation
C1(OP(O)OC2C=CC=CC=2)C=CC=CC=1.[CH:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[C:19]([OH:26])[CH:18]=1.[NH:27]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:28][C:29](O)=[O:30]>N1C=CC=CC=1>[N+:23]([C:22]1[CH:21]=[CH:20][C:19]([O:26][C:29](=[O:30])[CH2:28][NH:27][C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])=[CH:18][CH:17]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 14349BenzyloxycarbonylglycineHCID 426896Phosphorous diphenyl ester

Product 1

HCID 15616N-((Phenylmethoxy)carbonyl)glycine 4-nitrophenyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent4×

Procedure

A mixture of 2.93 g. (0.0125 mole) of phosphorous diphenyl ester and 3.37 g. (0.0125 mole) of mercuric chloride was refluxed for 1 hour in 20 ml. of pyridine. Thereafter, 1.74 g. (0.0125 mole) of p-nitrophenol and 10 ml. of pyridine were added, and the mixture was further reacted for 1 hour. To the reaction mixture were added 2.61 g. (0.0125 mole) of Z-Gly. OH having an amino group protected with Z and 10 ml. of pyridine, and the mixture was reacted under reflux for 1 hour. After completion of the reaction, pyridine was removed by distillation under reduced pressure, and the residue was extracted with 100 ml. of ethyl acetate. The ethyl acetate layer was washed with 2N--HCl, a saturated aqueous NaHCO3 solution and water in this order and then dried over anhydrous Na2SO4, and thereafter ethyl acetate was removed by distillation under reduced pressure. The resulting residue was allowed to stand to form a solid, which was then recrystallized from ethanol to obtain N-benzyloxycarbonyl glycine p-nitrophenyl ester (hereinafter represented by ##SPC6##

Workup

  1. additionA mixture of 2.93 g
  2. customthe mixture was further reacted for 1 hour
  3. additionTo the reaction mixture were added 2.61 g
  4. temperatureunder reflux for 1 hour
  5. customwas removed by distillation under reduced pressure
  6. extractionthe residue was extracted with 100 ml
  7. washThe ethyl acetate layer was washed with 2N
  8. dry with materialHCl, a saturated aqueous NaHCO3 solution and water in this order and then dried over anhydrous Na2SO4
  9. customethyl acetate was removed by distillation under reduced pressure
  10. customto form a solid, which
  11. customwas then recrystallized from ethanol

Sources & evidence

ORD record
ord-7f0fff29f3874cfb8a398bcae10b0ec3
Source dataset
uspto-grants-1976_08
Patent number
US03974219

Linked notes

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