Dicyclohexylcarbodiimide → HCID 22867564, compound

HRID 1489773Notes

Reaction equation

HRID 1489773 reaction equation
[C:1]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][C:16](=O)[NH2:17])(=[O:12])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[C:1]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][C:16]#[N:17])(=[O:12])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 11044384(S)-4-Amino-4-oxo-2-(((quinolin-2-yl)carbonyl)amino)butanoic acid

Product 1

HCID 22867564HCID 22867564, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 0.198 g (0.69 mmol) of N-quinaldoyl-L-asparagine and 0.24 ml (1.38 mmol) of N,N-diisopropylethylamine in 1 ml of chloroform was added 0.146 g (0.71 mmol) of dicyclohexylcarbodiimide. The reaction mixture was stirred for 24 hr. at room terperature, then partitioned between 10ml of 5% sodium bicarbonate and 10 ml of ether. The aqueous phase was acidified to pH2 and the acid was taken up by extraction with chloroform (3×10ml). The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to give 0.101 g of crude product. This was recrystallized from a small portion of methylene chloride to give 0.06 g of the title compound melting at 144°-146° C.; NMR (5% DMSO-d6 in CDCl3): 3.22 (d, 2H, ala CH2); 4.95 (m, 1H, ala CH); 7.2-8.57 (m, 7H, aromatic, OH); 9.19(d, 1H, NH).

Workup

  1. customat room terperature, then partitioned between 10ml of 5% sodium bicarbonate and 10 ml of ether
  2. extractionthe acid was taken up by extraction with chloroform (3×10ml)
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give 0.101 g of crude product
  7. customThis was recrystallized from a small portion of methylene chloride

Sources & evidence

ORD record
ord-7bcb0029dcf746f0a383e6413a353871
Source dataset
uspto-grants-1997_10
Patent number
US05679688

Reaction notes

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