Dicyclohexylcarbodiimide → HCID 13580544, compound

HRID 1380580Notes

Reaction equation

HRID 1380580 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:23])[CH2:18][CH2:19][C:20](O)=[O:21])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:24])[O:5][N:4]=1)[CH3:2].O[N:26]1[C:30](=O)CC[C:27]1=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([C:3]1[C:7]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[C:17](=[O:23])[CH2:18][CH2:19][C:20]([N:26]([CH3:30])[CH3:27])=[O:21])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:6]([CH3:24])[O:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 13520521HCID 13520521, compound

Product 1

HCID 13580544HCID 13580544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 978 mg (0.003 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-γ-oxo-indole-3-butanoic acid in 15 ml of methylene chloride is treated with 345 mg (0.003 mole) of N-hydroxy-succinimide followed by the dropwise addition of 618 mg (0.003 mole) of dicyclohexylcarbodiimide in 10 ml CH2Cl2. The resulting mixture is stirred 5 hours at room temperature. The mixture is then filtered, and the filter cake is washed with CH2Cl2. The combined CH2Cl2 layers are added dropwise to 20 ml of 40% aqueous dimethylamine and 20 ml of CH2Cl. The mixture is stirred overnight; following which water is added and the layers separated. The CH2Cl2 layer is washed with water, brine, dried over MgSO4, filtered and evaporated. The residue is crystallized to give the title compound, m.p. 144.5°-148° C.

Workup

  1. filtrationThe mixture is then filtered
  2. washthe filter cake is washed with CH2Cl2
  3. additionThe combined CH2Cl2 layers are added dropwise to 20 ml of 40% aqueous dimethylamine and 20 ml of CH2Cl
  4. stirringThe mixture is stirred overnight
  5. additionis added
  6. customthe layers separated
  7. washThe CH2Cl2 layer is washed with water, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is crystallized

Sources & evidence

ORD record
ord-77d10de2a2674665b9fae5250b95f7ab
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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