Dicyclohexylcarbodiimide → HCID 131717493, compound

HRID 847301Notes

Reaction equation

HRID 847301 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.Cl.[NH2:20][NH:21][C:22]([NH2:24])=[O:23].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C(N(CC)CC)C>[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]([NH:20][NH:21][C:22]([NH2:24])=[O:23])=[O:5]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11236Semicarbazide hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 131717493HCID 131717493, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of Cbz-Pro (1.25 g), semicarbazide hydrochloride (5.5 g), and HOBt (6.75 g) in DMF (100 mL) is added triethylamine (7.5 mL) and DCC (10.5 g) at 0° C. with stirring. The reaction is stirred at 0° C. for 24 hours. The precipitate is filtered and the filtrate is concentrated in vacuo. The residue is triturated with saturated NaHCO3 solution, filtered, washed with water and dried to give Cbz-Pro-azaGlyNH2. Cbz-Pro-azaGlyNH2 (10 g) is catalytically hydrogenated in (1:1) methanol/DMF at pH 4.5 in the presence of Pd catalyst. At the end of the hydrogenation the catalyst is filtered and the filtrate is concentrated in vacuo to give H-Pro-azaGlyNH2.HCl. To a solution of H-Pro-azaGlyNH2.HCl (2.08 g), HOBt (1.63 g), and Boc-Lys(N,N-epsilon-isopropyl,Cbz)-OH (1.26 g) in DMF (40 mL), DCC (2.1 g) is added with stirring at 0° C. for 2 hours and then at 4° C. for 24 hours. After workup and trituration with ether Boc-Lys(N,N-epsilon-isopropyl,Cbz)-Pro-azaGlyNH2 is obtained.

Workup

  1. stirringThe reaction is stirred at 0° C. for 24 hours
  2. filtrationThe precipitate is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe residue is triturated with saturated NaHCO3 solution
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9bde58ff039548bc8d7d737024727016
Source dataset
uspto-grants-1992_08
Patent number
US05140009

Reaction notes

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