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Heptane → ethanesulfonic acid (3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl)methylamide

HRID 634616
Notes
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Reaction equation

HRID 634616 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH3:7])(=[O:5])=[O:4].[H-].[Na+].[CH3:10][C:11]1([CH3:22])[O:20][C:19]2[C:14](=[CH:15][N:16]=[CH:17][CH:18]=2)[CH:13]2[O:21][CH:12]12.CCCCCCC>CS(C)=O.C(OCC)(=O)C>[OH:21][CH:12]1[C:11]([CH3:22])([CH3:10])[O:20][C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH:13]1[CH2:1][NH:2][S:3]([CH2:6][CH3:7])(=[O:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8900HeptaneHCID 24758Sodium hydrideHCID 108560303,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridineHCID 11105495N-methylethane-1-sulfonamide

Product 1

HCID 86756350ethanesulfonic acid (3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl)methylamideYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 480 mg (3.5 mmol) of N-methylethylsulfonamide in 0.75 ml DMSO (dimethylsulfoxide) is added to a suspension of 27 mg (0.7 mmol) of NaH (60% strength) in 1.5 ml of DMSO. After stirring at room temperature for 2 h, a solution of 0.48 g (2.7 mmol) of 2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-6-aza-cyclo-propa[a]naphthalene (prepared analogously to G. Burell et al. J. Med. Chem. 33 (1990) 3023-3027) in 6 ml of DMSO is added dropwise. The mixture is heated at 60° C. for 4 h and then stirred overnight at room temperature. The reaction mixture is added to ice water and extracted with ethyl acetate. After removing the solvent in vacuo, the solid obtained is stirred with a mixture of heptane and ethyl acetate and filtered off with suction. 400 mg (67%) of ethanesulfonic acid (3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-pyrano[3,2-c]pyridin-4-yl)methylamide are obtained as a solid (m.p. 163° C.).

Workup

  1. temperatureThe mixture is heated at 60° C. for 4 h
  2. stirringstirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. customAfter removing the solvent in vacuo
  5. customthe solid obtained
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-da3477a59af8404382f80ebffa92d067
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06184221B2

Reaction notes

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