Oxalyl chloride → HCID 9950389, compound

HRID 1839176Notes

Reaction equation

HRID 1839176 reaction equation
[CH3:1][C:2]([NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=3[O:16][C:15]=2[CH:23]=1)(=[O:10])=[O:9])([CH3:6])[C:3](O)=[O:4].C(Cl)(=O)C(Cl)=O.Cl.[NH2:31][OH:32].C(=O)(O)[O-].[Na+]>ClCCCl.CN(C)C=O.O1CCCC1>[OH:32][NH:31][C:3](=[O:4])[C:2]([CH3:6])([NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]2[C:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=3[O:16][C:15]=2[CH:23]=1)(=[O:10])=[O:9])[CH3:1]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 9905824HCID 9905824, compound

Product 1

HCID 9950389HCID 9950389, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-2-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonylamino)-propionic acid (387 mg, 1.15 mmol) was suspended in 1,2-dichloroethane (22 mL), then oxalyl chloride (438 mg, 3.45 mmol) was added dropwise. N,N-dimethylformamide (2 drops) was added and a gas evolved from the solution. The reaction was stirred until the solids were dissolved. The reaction mixture was concentrated by evaporation, washed with hexane, concentrated again, and dissolved in tetrahydrofuran (20 mL), then added to an aqueous tetrahydrofuran solution (1:1, 34 mL, 5° C.) of hydroxylamine hydrochloride (800 mg, 11.5 mmol) and sodium bicarbonate (1.8 g, 17.25 mmol). The reaction was stirred, warming up to room temperature, overnight. The tetrahydrofuran was removed from the reaction mixture in vacuo. To the residue, 1 M HCl and dichloromethane were added. The organic phase was separated from the organic phase, dried (over MgSO4), and concentrated. The crystals were rinsed with ethyl acetate, then collected by filtration to give N-hydroxy-2-methyl-2-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonylamino)-propionamide (a compound of general Formula IX) (235 mg, 58%), the structure of which is shown below. The melting point of this compound was determined to be 175-176° C. 1HNMR (CDCl3): δ10.0 (s, 1H), 7.6 (s, 1H), 7.4 (d, 1H), 7.2 (m, 2H), 2.6 (m, 2H), 2.4 (m, 2H) 1.6 (m, 4H), 1.0 (s, 6H) ppm.

Workup

  1. dissolutionwere dissolved
  2. concentrationThe reaction mixture was concentrated by evaporation
  3. washwashed with hexane
  4. concentrationconcentrated again
  5. dissolutiondissolved in tetrahydrofuran (20 mL)
  6. stirringThe reaction was stirred
  7. customThe tetrahydrofuran was removed from the reaction mixture in vacuo
  8. additionTo the residue, 1 M HCl and dichloromethane were added
  9. customThe organic phase was separated from the organic phase
  10. dry with materialdried (over MgSO4)
  11. concentrationconcentrated
  12. washThe crystals were rinsed with ethyl acetate
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-bb0f2ba8d29749c189f9c51d295a5e30
Source dataset
uspto-grants-2004_01
Patent number
US06677355B1

Reaction notes

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