Dicyclohexylcarbodiimide → HCID 18603232, compound

HRID 1982649Notes

Reaction equation

HRID 1982649 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].OC1C2N=NNC=2C=CC=1.[C:17]([NH:24][C@@H:25]([C:30]([OH:32])=O)[CH2:26][CH:27]([CH3:29])[CH3:28])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.C(N(CC)CC)C>[C:17]([NH:24][C@@H:25]([C:30]([NH:2][CH2:3][C:4]([NH2:6])=[O:5])=[O:32])[CH2:26][CH:27]([CH3:28])[CH3:29])([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 2723639Glycinamide hydrochlorideHCID 2724763BOC-D-LEU-OH H2OHCID 178418300HCID 178418300, compound

Product 1

HCID 18603232HCID 18603232, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1.55 g (0.014 mole) of glycinamide hydrochloride is dissolved in 50 ml of DMF by warming to 50°. The solution is cooled to 25° and 2 ml of triethylamine is added, followed by 1.89 g of hydroxybenztriazole, 3.5 g (0.014 mol) of BOC-D-leucine H2O and lastly, 2.9 g (0.014 mol) of dicyclohexylcarbodiimide. The mixture is stirred two days at 25° and then evaporated in vacuo to an oil. The oil is dissolved in 200 ml EtOAC, 50 ml CHCl3. The organic solution is washed with water, 20% citric acid solution, water, 10% Na2CO3 solution. The EtOAc solution is dried over MgSO4 and the solvent removed in vacuo to a glass, 3.7 g (93%).

Workup

  1. temperatureby warming to 50°
  2. temperatureThe solution is cooled to 25°
  3. customevaporated in vacuo to an oil
  4. dissolutionThe oil is dissolved in 200 ml EtOAC, 50 ml CHCl3
  5. washThe organic solution is washed with water, 20% citric acid solution, water, 10% Na2CO3 solution
  6. dry with materialThe EtOAc solution is dried over MgSO4
  7. customthe solvent removed in vacuo to a glass, 3.7 g (93%)

Sources & evidence

ORD record
ord-b1cf025d323e486bac7fa0720522d659
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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