Dicyclohexylcarbodiimide → HCID 178489085, compound

HRID 2210484Notes

Reaction equation

HRID 2210484 reaction equation
[OH:1][N:2]=[C:3]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:4]([NH:6][C@H:7]([C:21](O)=[O:22])[CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)=[O:5].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.C([O-])(=O)C.[Na+]>C(OCC)C.C(O)(=O)C.O1CCOCC1>[OH:22][C:21]1[N+:2]([O-:1])=[C:3]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:4](=[O:5])[NH:6][C:7]=1[CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 517045Sodium AcetateHCID 86749042HCID 86749042, compound

Product 1

HCID 178489085HCID 178489085, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a dioxane solution (200 ml) containing 18.71 of N-(2-hydroxyimino-4-methylpentanoyl)-(3,4,5-trimethoxy)phenylalanine and 6.04 g of N-hydroxysuccinimide, was added 18.83 g of N,N'-dicyclohexylcarbodiimide, and the mixture was stirred at room temperature for 12 hours. After the reaction mixture was filtered, to the filtrate thus obtained was added 4.31 g of sodium acetate, then this mixture was stirred at room temperature for 5 hours. Then the reaction mixture was transferred to 600 ml of ice-water containing 5 ml of acetic acid, the precipitated semi-solid was collected and was dissolved in dichloromethane, the insoluble matters were removed by filtration, the organic layer was washed with in aqueous solution saturated with sodium chloride, then dried with magnesium sulfate. The solvent was removed by distillation to obtain yellow semi-solid, then 30 ml of diethyl ether was added and the mixture was allowed to stand for 2 days in a refrigerator to crystallize. The solid matter was collected by filtration and washed with diethyl ether to obtain 6.11 g of 5-hydroxy-3-isobutyl- 6-(3,4,5-trimethoxybenzyl)-1,2-dihydropyrazin-2-one 4-oxide as yellow powder.

Workup

  1. filtrationAfter the reaction mixture was filtered, to the filtrate
  2. customthus obtained
  3. stirringthis mixture was stirred at room temperature for 5 hours
  4. customthe precipitated semi-solid was collected
  5. dissolutionwas dissolved in dichloromethane
  6. customthe insoluble matters were removed by filtration
  7. washthe organic layer was washed with in aqueous solution saturated with sodium chloride
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was removed by distillation
  10. customto obtain yellow semi-solid
  11. waitto stand for 2 days in a refrigerator
  12. customto crystallize
  13. filtrationThe solid matter was collected by filtration
  14. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c035736114b04ee58c27f58dec64ecb0
Source dataset
uspto-grants-1995_10
Patent number
US05459142

Reaction notes

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