N,N'-Dicyclohexylurea → 2-((tert-butoxy)carbonylamino)-3-hydroxy-N-(4-methyl-2-oxo(2H-chromen-7-yl))propanamide

HRID 378529Notes

Reaction equation

HRID 378529 reaction equation
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:27])=[CH:21][C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O>C(Cl)Cl>[C:4]([O:3][C:1]([NH:8][CH:9]([CH2:10][OH:11])[C:12]([NH:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:27])=[CH:21][C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1)=[O:14])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 922497-Amino-4-methylcoumarinHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 178418300HCID 178418300, compound

Product 1

HCID 193542182-((tert-butoxy)carbonylamino)-3-hydroxy-N-(4-methyl-2-oxo(2H-chromen-7-yl))propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Briefly, 1.1 mmol N-BOC-L-Serine (Fluka) is dissolved in 2 ml methylene chloride. Then 1.1 mmol 7-Amino-4-methylcoumarin and 1.2 mmol hydroxybenztriazole are added with stirring. Over a period of 30 minutes, a solution of 1.3 mmol dicyclohexyl carbodiimide in 1.4 ml methylene chloride is added dropwise. The reaction is stirred at room temperature for 20 hours, during which time a precipitate of dicyclohexylurea forms. The precipitate is removed by filtration and washed with methylene chloride. The combined solutions (filtrates) are evaporated under reduced pressure and the residue chromatographed over silica gel with methylene chloride--ethylacetate as the eluent yielding 2-((tert-butoxy)carbonylamino)-3-hydroxy-N-(4-methyl-2-oxo(2H-chromen-7-yl))propanamide.

Workup

  1. customThe precipitate is removed by filtration
  2. washwashed with methylene chloride
  3. customThe combined solutions (filtrates) are evaporated under reduced pressure
  4. customthe residue chromatographed over silica gel with methylene chloride

Sources & evidence

ORD record
ord-c29c3934039c432d8f58df9f7451c331
Source dataset
uspto-grants-2000_02
Patent number
US06031094

Reaction notes

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