Dicyclohexylcarbodiimide → HCID 70538604, compound

HRID 1277801Notes

Reaction equation

HRID 1277801 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:22])[C:16](=[CH:20][CH:21]=2)[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=1)=[O:5])[CH3:3].[C:23]([NH:26][C@H:27]([C:29](O)=[O:30])[CH3:28])(=[O:25])[CH3:24].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:23]([NH:26][C@H:27]([C:29]([NH:1][C@H:2]([C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[NH:14][C:15](=[O:22])[C:16](=[CH:20][CH:21]=2)[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=1)=[O:5])[CH3:3])=[O:30])[CH3:28])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 88064N-Acetyl-L-alanineHCID 53958365HCID 53958365, compound

Product 1

HCID 70538604HCID 70538604, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.50 g (15 mM) of 6-[4-(L-alanylamino)-phenyl]-1,2-dihydro-2-oxonicotinic acid, Example 4, 1.97 g (15 mM) N-acetyl-L-alanine, 2.02 g (15 mM) 1-hydroxybenzotriazole, and 150 ml of DMF was stirred at room temperature and 3.09 g (15 mM) of dicyclohexylcarbodiimide was added. After 19 hours the reaction mixture was filtered and the filtrate evaporated to dryness. Water was added and the solids filtered, washed with hot ethyl acetate and ether, and dried, giving 5.01 g of 6-[4-(N-acetyl-L-alanyl-L-alanylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid.

Workup

  1. filtrationAfter 19 hours the reaction mixture was filtered
  2. customthe filtrate evaporated to dryness
  3. additionWater was added
  4. filtrationthe solids filtered
  5. washwashed with hot ethyl acetate and ether
  6. customdried

Sources & evidence

ORD record
ord-da4a489ef43f4e9d910cef5e81a2d647
Source dataset
uspto-grants-1981_07
Patent number
US04278681

Reaction notes

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