Benzyl chloroformate → HCID 54425150, compound

HRID 1419722Notes

Reaction equation

HRID 1419722 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[N:10]([C:11](=[O:33])[C@@H:12]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6]1=[O:38].C([O-])(O)=O.[Na+].[CH:44]1[CH:49]=[CH:48][C:47]([CH2:50][O:51][C:52](Cl)=[O:53])=[CH:46][CH:45]=1>O1CCOCC1>[CH2:26]([O:25][C:23]([NH:22][C@@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:11]([N:10]1[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6](=[O:38])[C@@H:5]1[CH2:4][CH2:3][CH2:2][NH:1][C:52]([O:51][CH2:50][C:47]1[CH:48]=[CH:49][CH:44]=[CH:45][CH:46]=1)=[O:53])=[O:33])=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 54085635HCID 54085635, compound

Product 1

HCID 54425150HCID 54425150, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 100 ml of a 50% aqueous solution of dioxane was dissolved 3.8 g of (S,S)-3-(3-aminopropyl)-4-[2-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionyl]-2-oxopiperazine-1-acetic acid produced in Reference Example 33. To the solution was added 1.52 g of NaHCO3, to which was added dropwise, under ice-cooling, 1.24 ml of Z-chloride. The mixture was stirred for 1.5 hour at room temperature. Dioxane was distilled off. To the residue was added a 3% aqueous solution of KHSO4 to adjust the pH to 2. The mixture was subjected to extraction with ethyl acetate. The extract solution was washed with a saturated aqueous solution of NaHCO3 and dried (Na2SO4), followed by concentration under reduced pressure. To the concentrate was added ether. The mixture was subjected to decantation twice to afford 4 g of the title compound.

Workup

  1. customproduced in Reference Example 33
  2. additionto which was added dropwise, under ice-
  3. temperaturecooling
  4. distillationDioxane was distilled off
  5. additionTo the residue was added a 3% aqueous solution of KHSO4
  6. extractionThe mixture was subjected to extraction with ethyl acetate
  7. washThe extract solution was washed with a saturated aqueous solution of NaHCO3
  8. dry with materialdried (Na2SO4)
  9. concentrationfollowed by concentration under reduced pressure
  10. additionTo the concentrate was added ether

Sources & evidence

ORD record
ord-a11bf45773b94f20ab50e64389dc499b
Source dataset
uspto-grants-1999_03
Patent number
US05888531

Reaction notes

Loading…