4-Nitrophenol → N-Carbobenzoxy-beta-Benzyl-L-Aspartyl-L-Proline p-Nitrophenyl Ester

HRID 249069

Reaction equation

HRID 249069 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[C:11]([NH:21][C@H:22]([C:34]([N:36]1[CH2:43][CH2:42][CH2:41][C@H:37]1[C:38](O)=[O:39])=[O:35])[CH:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24](=[O:26])[OH:25])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][C:38](=[O:39])[C@@H:37]2[CH2:41][CH2:42][CH2:43][N:36]2[C:34](=[O:35])[C@H:22]([CH:23]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:24](=[O:25])[OH:26])[NH:21][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 54163294HCID 54163294, compound

Product 1

HCID 53695211N-Carbobenzoxy-beta-Benzyl-L-Aspartyl-L-Proline p-Nitrophenyl Ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

p-Nitrophenol (3.0 Kg) is added to the concentrated ethyl acetate solution of N-carbobenzoxy-β-benzyl-L-aspartyl-L-proline prepared as described in Example II above. The solution is cooled below 5° C. Dicyclohexylcarbodiimide (4.5 Kg) is dissolved in ethyl acetate (10-20 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 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 hot isopropyl alcohol (50-70 L) and cooled below 25° C. The solids are collected on a filter, rinsed with isopropyl alcohol and dried below 40° C. Melting point=88°-91° C.; specific rotation=-70° to -73° (C=1, ethyl acetate).

Workup

  1. customprepared
  2. temperatureThe solution is cooled below 5° C
  3. additionadded
  4. temperaturemaintaining the temperature below 5° C
  5. waitfor three hours at 20°-30° C
  6. customThe dicyclohexylurea is removed by filtration
  7. washwashed with ethyl acetate (20-30 L)
  8. concentrationThe filtrate is concentrated in vacuo below 60° C
  9. dissolutionThe concentrate is dissolved in hot isopropyl alcohol (50-70 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=-70° to -73° (C=1, ethyl acetate)

Sources & evidence

ORD record
ord-7363ea10945247a4944f8080ab782600
Source dataset
uspto-grants-1993_05
Patent number
US05212287

Linked notes

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