4-Nitrophenol → HCID 53721982, compound

HRID 249067Notes

Reaction equation

HRID 249067 reaction equation
[C:1]([NH:11][C@H:12]([C:24]([OH:26])=[O:25])[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH:27]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][CH:30]=[C:29](O)[CH:28]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[N+:33]([C:32]1[CH:27]=[CH:28][C:29]([O:25][C:24](=[O:26])[C@H:12]([CH:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([OH:16])=[O:15])[NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])=[CH:30][CH:31]=1)([O-:35])=[O:34]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 53769026N-carbobenzoxy-beta-benzyl-L-aspartic acid

Product 1

HCID 53721982HCID 53721982, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

N-carbobenzoxy-β-benzyl-L-aspartic acid (12 Kg) and p-nitrophenol (5.1 Kg) are dissolved in ethyl acetate (20-30 L) and the solution is cooled to below 5° C. Dicyclohexyl-carbodiimide (7.6 Kg) is dissolved in ethyl acetate (8-12 L) and added, maintaining the temperature below 5° C. The solution is stirred at reduced temperature for two hours and then for three hours at 20°-30° C. The dicyclohexylurea byproduct is removed by filtration and washed with ethyl acetate (20-30 L). The filtrate is concentrated in vacuo below 60° C. The concentrate is dissolved in a mixture of hot isopropyl alcohol (25-40 L) and distilled water (2-5 L) and cooled below 25° C. The solids are collected on a filter, rinsed with isopropyl alcohol and dried below 40° C. Melting point=76°-79° C.; specific rotation=-15° to 18° (C=1, DMF).

Workup

  1. temperaturethe solution is cooled to below 5° C
  2. additionadded
  3. temperaturemaintaining the temperature below 5° C
  4. waitfor three hours at 20°-30° C
  5. customThe dicyclohexylurea byproduct is removed by filtration
  6. washwashed with ethyl acetate (20-30 L)
  7. concentrationThe filtrate is concentrated in vacuo below 60° C
  8. dissolutionThe concentrate is dissolved in a mixture of hot isopropyl alcohol (25-40 L)
  9. distillationdistilled water (2-5 L)
  10. temperaturecooled below 25° C
  11. customThe solids are collected on a filter
  12. washrinsed with isopropyl alcohol
  13. customdried below 40° C
  14. customspecific rotation=-15° to 18° (C=1, DMF)

Sources & evidence

ORD record
ord-4a759e4379ae4150a7a57155d61f5fdd
Source dataset
uspto-grants-1993_05
Patent number
US05212287

Reaction notes

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