Dicyclohexylcarbodiimide → HCID 178427574, compound

HRID 1106953Notes

Reaction equation

HRID 1106953 reaction equation
[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:2]([C:28]([OH:30])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:27])[NH:8][S:9]([C:12]1[C:25]([CH3:26])=[C:23]([CH3:24])[C:22]2[O:21][C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:11])=[O:10].C1CCC([N:47]=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C@H:2]([C:28]([NH2:47])=[O:30])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:27])[NH:8][S:9]([C:12]1[C:25]([CH3:26])=[C:23]([CH3:24])[C:22]2[O:21][C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 178427583HCID 178427583, compound

Product 1

HCID 178427574HCID 178427574, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A] Z-Arg(Pmc)-OH (2.87 g, 5 mmoles) was dissolved in 15 ml of DMF, then added with 0.837 g (5.5 mmoles) of HOBT ammonium salt, and the reaction mixture was cooled to 0° C. After the addition of 1.135 g (5.5 mmoles) of DCC, the reaction mixture was brought to room temperature and kept under stirring for 300 minutes. After filtering dicyclohexylurea off, the solvent was evaporated under vacuum and the residue taken up in 25 ml of ethyl acetate and washed with an aqueous solution of 5% sodium hydrocarbonate, then with water till neutrality. The organic phase was anhydrified, the solvent evaporated under vacuum and the residue crystallized from ethyl ether/n-hexane. There were obtained 2.8 g of Z-Arg(Pmc)-NH2 [HPLC (gradient from 20 to 60% of B in A for 20 minutes): R.t. 15.7 min.; purity 98%].

Workup

  1. customwas brought to room temperature
  2. filtrationAfter filtering dicyclohexylurea off, the solvent
  3. customwas evaporated under vacuum
  4. washwashed with an aqueous solution of 5% sodium hydrocarbonate
  5. customthe solvent evaporated under vacuum
  6. customthe residue crystallized from ethyl ether/n-hexane

Sources & evidence

ORD record
ord-7e194c87516b42629322019c251ef187
Source dataset
uspto-grants-2000_05
Patent number
US06057295

Reaction notes

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