Phenyl isocyanate → HCID 54139436, compound

HRID 2413732Notes

Reaction equation

HRID 2413732 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[OH-].[Na+]>[C:21]1([NH:27][C:28]([NH:1][C@H:2]([C:4]([N:6]2[CH2:20][CH2:19][CH2:18][C@H:7]2[C:8]([N:10]2[CH2:17][CH2:16][CH2:15][C@H:11]2[C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 1155826522049-75-8

Product 1

HCID 54139436HCID 54139436, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

L-alanyl-L-prolyl-L-proline (3.00 g, 10.6 m mole) was dissolved in 1N aqueous sodium hydroxide (10.6 ml, 10.6 m mole), and phenylisocyanate (1.89 g, 15.9 m mole) was gradually added thereto while stirring and coating with ice. After that, the reaction solution was stirred overnight at room temperature. The pH value of the solution was about 7 and white crystals were given in the solution. The solution was adjusted to pH 12 with 1N aqueous sodium hydroxide and the insoluble matters were filtered off. The filtrate was washed with two 50 ml portions of ether and 6N hydrochloric acid was added thereto to adjust the pH value to 1.0. The solution was extracted with two 100 ml portions of ethyl acetate in order to separate the products. The ethyl acetate layer was washed with 10% aqueous sodium chloride, dried over anhydrous sodium sufate, and concentrated under reduced pressure. To the thus concentrated matter with crystals, ether was added to effect further crystallization. The crystals were obtained by filtration and dried to give N-phenylcarbamoyl-L-alanyl-L-prolyl-L-proline (2.50 g).

Workup

  1. stirringAfter that, the reaction solution was stirred overnight at room temperature
  2. filtrationthe insoluble matters were filtered off
  3. washThe filtrate was washed with two 50 ml portions of ether and 6N hydrochloric acid
  4. additionwas added
  5. extractionThe solution was extracted with two 100 ml portions of ethyl acetate in order
  6. customto separate the products
  7. washThe ethyl acetate layer was washed with 10% aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sufate
  9. concentrationconcentrated under reduced pressure
  10. additionTo the thus concentrated matter with crystals, ether was added
  11. customcrystallization
  12. customThe crystals were obtained by filtration
  13. customdried

Sources & evidence

ORD record
ord-f24c66f6b27b478a8be31257c8276079
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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