Dicyclohexylcarbodiimide → HCID 131730148, compound

HRID 1801973Notes

Reaction equation

HRID 1801973 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:29]([N:36]1[C:48]2[C:47]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[N:41]=[C:40](N)[C:39]=2[N:38]=[CH:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(N(CC)CC)C>[C:6]([N:8]([CH2:9][C:10]([OH:12])=[O:11])[CH3:13])([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7].[CH2:29]([N:36]1[C:48]2[C:47]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[N:41]=[C:40]([C:6]([NH2:8])=[O:5])[C:39]=2[N:38]=[CH:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 11231149HCID 11231149, compound

Product 1

HCID 131730148HCID 131730148, compoundYield 134.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

18.9 g (0.1 mol) of N-t-Butyloxycarbonyl-N-methylglycine was dissolved in 300 ml of dichloromethylene. 20.6 g of N,N′-Dicyclohexylcarbodiimide was added into the reaction mixture. The mixture was stirred for 1 hour at 0° C. 32.2 g (0.1 mol) of 1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine and 20 ml of triethylamine were added into the reaction mixture. The mixture was stirred for 3 hours at RT. The solid was removed by filtration. The dichloromethylene solution was washed with water (1×100 ml), 30% citric acid (1×100 ml), water (1×100 ml), 5% NaHCO3 (2×100 ml), and water (3×100 ml). The organic solution was dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration. The organic solution was evaporated to dryness. After drying, it yielded 33 g of the desired product (74.1%). Elementary analysis: C25H27N5O3; MW: 445.51; calculated % C, 67.40; H, 6.11; N, 15.72; O: 10.77. found % C, 67.35; H, 6.14; N, 15.70; O: 10.81.

Workup

  1. stirringThe mixture was stirred for 3 hours at RT
  2. customThe solid was removed by filtration
  3. washThe dichloromethylene solution was washed with water (1×100 ml), 30% citric acid (1×100 ml), water (1×100 ml), 5% NaHCO3 (2×100 ml), and water (3×100 ml)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. customThe organic solution was evaporated to dryness
  7. customAfter drying

Sources & evidence

ORD record
ord-6353578aa4b34f87b45737f33fb34f70
Source dataset
uspto-grants-2013_01
Patent number
US08349866B2

Reaction notes

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