Dicyclohexylcarbodiimide → HCID 14723607, compound

HRID 1722331Notes

Reaction equation

HRID 1722331 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[S:17][C:16]([S:18][CH2:19][C:20](O)=[O:21])=[N:15][N:14]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[OH:44][N:45]1[C:49]2C=CC=CC=2N=N1.Cl.CNO>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C.O1CCCC1>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[S:17][C:16]([S:18][CH2:19][C:20]([N:45]([OH:44])[CH3:49])=[O:21])=[N:15][N:14]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

9

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77906N-methylhydroxylamine hydrochlorideHCID 128491YM 16638

Product 1

HCID 14723607HCID 14723607, compoundYield 36.8%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 0.5 g of [[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid obtained in example 22, 0.23 g of dicyclohexylcarbodiimide, 0.14 g of 1-hydroxybenzotriazole, and 50 ml of tetrahydrofuran was added a mixture of 0.27 g of N-methylhydroxylamine.hydrochloride, 0.3 g of triethylamine, and 5 ml of N,N-dimethylformamide and the resultant mixture was stirred overnight at room temperature. Then, insoluble matters were filtered off and the filtrate thus formed was concentrated under reduced pressure. To the residue thus formed was added 100 ml of ethyl acetate and the mixture was washed with water, washed with a diluted aqueous solution of sodium hydrogencarbonate, and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate, then insoluble materials were filtered off and the filtrate formed was concentrated. The residue thus obtained was recrystallized from a mixture of toluene and n-hexane to provide 0.18 g of 2-[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]-N-hydroxy-N-methylacetamide.

Workup

  1. additionwas added
  2. filtrationThen, insoluble matters were filtered off
  3. customthe filtrate thus formed
  4. concentrationwas concentrated under reduced pressure
  5. customTo the residue thus formed
  6. washthe mixture was washed with water
  7. washwashed with a diluted aqueous solution of sodium hydrogencarbonate, and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customTo the residue thus obtained
  11. filtrationinsoluble materials were filtered off
  12. customthe filtrate formed
  13. concentrationwas concentrated
  14. customThe residue thus obtained
  15. customwas recrystallized from a mixture of toluene and n-hexane

Sources & evidence

ORD record
ord-ad415fb2601947da824b02e54269f64c
Source dataset
uspto-grants-1989_08
Patent number
US04855310

Reaction notes

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