Sulfuryl chloride → Quinaldic Acid

HRID 1861628Notes

Reaction equation

HRID 1861628 reaction equation
C(OC(=O)N[C@H:8]([C:13](=O)[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19]NC[CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])C)(C)(C)C.S(Cl)(Cl)(=O)=[O:26]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[N:14]1[C:13]2[C:19](=[CH:12][CH:10]=[CH:9][CH:8]=2)[CH:20]=[CH:21][C:15]=1[C:16]([OH:22])=[O:26]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 12076054HCID 12076054, compound

Product 1

HCID 7124Quinaldic Acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of [(S)-1-(3-hydroxy-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert butyl ester of Example 1g (2.5 g, 7.28 mmol) in CH2Cl2 (100 mL) and sat. NaHCO3 (400 mL) was added the solution of 2-pyridinesulfonyl chloride-N-oxide (27 mL, 102 mg/mL) dropwise in portions. As the addition proceeds additional sat. NaHCO3 is added in order to maintain the pH at approximately 8-9. Upon complete addition of the sulfonylchloride the reaction is stirred for an additional hour whereupon the organic layer was removed and washed with brine. The organic layer was evaporated and the residue chromatographed (5% methanol:dichloromethane) to provide 2.5 g of the title compound: MS (El) 500 (M+H+).

Workup

  1. additionAs the addition
  2. additionis added in order
  3. temperatureto maintain the pH at approximately 8-9
  4. customwas removed
  5. washwashed with brine
  6. customThe organic layer was evaporated
  7. customthe residue chromatographed (5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-bfb0d094135f47f0abfa3a4227f00f23
Source dataset
uspto-grants-2003_03
Patent number
US06534498B1

Reaction notes

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