Dicyclohexylcarbodiimide → HCID 21970706, compound

HRID 1952730Notes

Reaction equation

HRID 1952730 reaction equation
[C:1]([NH:8][C@@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N[C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[C:21]([C:1]([NH2:8])=[O:2])[CH:22]=1.[C:1]([NH:8][C@@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 113753-AminoquinolineHCID 637610Boc-D-phenylalanine

Product 1

HCID 21970706HCID 21970706, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-Boc-D-phenylalanine (1.25 g, 4.7 mmol) in ethyl acetate (40 mL) was treated sequentially with 3-aminoquinoline (1.4 g, 9.4 mmol) and dicyclohexylcarbo-diimide (1.02 g, 4.9 mmol). The reaction mixture was stirred at room temperature for 16 hr, filtered and the filtrate washed with 1M hydrochloric acid (2×25 mL), saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford titled compound (950 mg) as an oil.

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with 1M hydrochloric acid (2×25 mL), saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7da7a4e367d6409389c5030fb54c865e
Source dataset
uspto-grants-2000_09
Patent number
US06114310

Reaction notes

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