4-Nitrophenol → HCID 12769077, compound

HRID 225104Notes

Reaction equation

HRID 225104 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])(=[O:3])[CH3:2].[CH:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20](O)[CH:19]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[C:1]([S:4][CH2:5][CH:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]([NH:9][CH2:10][C:11]([O:13][C:20]1[CH:19]=[CH:18][C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=1)=[O:12])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 12769072HCID 12769072, compound

Product 1

HCID 12769077HCID 12769077, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

N-[2-[(Acetylthio)methyl]-4-methyl-1-oxopentyl]glycine (0.5 g) is dissolved in 30 ml of ethyl acetate along with p-nitrophenol (0.2 g). This solution is cooled to 5° C., N,N'-dicyclohexylcarbodiimide (0.4 g) is added portionwise and the reaction mixture is stirred at 5° for about 16 hours. The dicyclohexyl urea is filtered off and the filtrate is concentrated thoroughly in vacuo. Isopropyl ether is added to the residue and allowed to sit for about 16 hours. The crystalline solid is filtered to yield 0.4 g of product, melting point 95°-100° C.

Workup

  1. filtrationThe dicyclohexyl urea is filtered off
  2. concentrationthe filtrate is concentrated thoroughly in vacuo
  3. additionIsopropyl ether is added to the residue
  4. waitto sit for about 16 hours
  5. filtrationThe crystalline solid is filtered

Sources & evidence

ORD record
ord-af002a0ed36d445a979544365e8ffadf
Source dataset
uspto-grants-1980_11
Patent number
US04235885

Reaction notes

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