Oxalyl chloride → HCID 10202316, compound

HRID 411130Notes

Reaction equation

HRID 411130 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([S:14]([N:17]2[CH2:22][CH2:21][S:20][C:19]([CH3:24])([CH3:23])[C@@H:18]2[C:25]([OH:27])=O)(=[O:16])=[O:15])[CH:2]=1.C(Cl)(=O)C(Cl)=O.Cl.[NH2:35][OH:36].C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[OH:36][NH:35][C:25]([C@H:18]1[C:19]([CH3:24])([CH3:23])[S:20][CH2:21][CH2:22][N:17]1[S:14]([C:3]1[CH:2]=[CH:1][C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=1)(=[O:16])=[O:15])=[O:27]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 10135944HCID 10135944, compound

Product 1

HCID 10202316HCID 10202316, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A dichloromethane solution of the acid synthesized in Example 1 (0.26 g, 0.64 mmol/10 mL CH2Cl2) was reacted with oxalyl chloride (0.1 mL, 0.77 mmol) and a catalytic amount of N,N-dimethylformamide under an atmosphere of nitrogen. After stirring at room temperature for 30 minutes, the solution was concentrated in vacuo. The crude acid chloride was dissolved in tetrahydrofuran and added to a tetrahydrofuran (60 mL)/water (20 mL) solution containing hydroxylamine hydrochloride (0.44 g, 6.4 mmol) and sodium bicarbonate (0.81 g, 9.6 mmol). The reaction mixture was stirred at room temperature overnight, then concentrated in vacuo. The crude product was diluted with ethyl acetate and washed with water, brine, dried (MgSO4), and concentrated. The resulting residue was recrystallized from hexane/ethyl acetate to give 0.14 g of the title compound.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe crude acid chloride was dissolved in tetrahydrofuran
  3. additionadded to a tetrahydrofuran (60 mL)/water (20 mL) solution
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. concentrationconcentrated in vacuo
  6. additionThe crude product was diluted with ethyl acetate
  7. washwashed with water, brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe resulting residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c4efde522476412887ddf8f66460402d
Source dataset
uspto-grants-2003_05
Patent number
US06559142B2

Reaction notes

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