Dicyclohexylcarbodiimide → HCID 131710622, compound

HRID 1415340Notes

Reaction equation

HRID 1415340 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH:19]1([NH-:22])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 131710622HCID 131710622, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 124.6 g (0.5 mol) of Z-Pro-OH, 34.8 ml of cyclopropyl amine and 67.5 g HOBt in 200 ml of absolute tetrahydrofurane 110 g of DCC were added at 0° C, the solution was stirred for one hour at 0° C and allowed to stand over night at room temperature. The deposit was suction-filtered and the filtrate was concentrated. The residue was taken up in ethyl acetate and extracted with saturated NaHCO3 -solution, 2N HCl, saturated NaHCO3 -solution and water, dried over Na2SO4 and concentrated. The residue was triturated with petroleum ether and suction-filtered. The ethyl acetate/petroleum ether was recrystallized.

Workup

  1. waitto stand over night at room temperature
  2. filtrationThe deposit was suction-filtered
  3. concentrationthe filtrate was concentrated
  4. extractionextracted with saturated NaHCO3 -solution, 2N HCl, saturated NaHCO3 -solution and water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was triturated with petroleum ether
  8. filtrationsuction-filtered
  9. customThe ethyl acetate/petroleum ether was recrystallized

Sources & evidence

ORD record
ord-d64a08f802bf4335ac1336d16c882538
Source dataset
uspto-grants-1977_01
Patent number
US04003884

Reaction notes

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