Water → HCID 59354925, compound

HRID 1099448Notes

Reaction equation

HRID 1099448 reaction equation
[H-].[Na+].[CH:3]1([SH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][N:11]=1.ClC1C=CC=C(C(OO)=[O:29])C=1.[OH2:32]>CN(C)C=O.C(OCC)(=O)C>[CH:3]1([S:8]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=2)(=[O:29])=[O:32])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

8

Reactant 5

HCID 962WaterHCID 15510CyclopentanethiolHCID 24758Sodium hydrideHCID 70297m-Chloroperbenzoic acidHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 59354925HCID 59354925, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.022 g, 0.55 mmol) was added to a solution of cyclopentanethiol (0.053 mL, 0.50 mmol) in N,N-dimethylformamide (0.7 mL). The reaction mixture was stirred under an atmosphere of nitrogen for 5 min. Ethyl 6-chloronicotinate (0.093 g, 0.5 mmol) was added, and the reaction mixture was stirred at ambient temp over night. Water and ethyl acetate were added, and the organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography using a gradient of ethyl acetate in heptane yielded a colourless oil. The crude was dissolved in N,N-dimethylformamide (1.7 mL) and added m-chloroperbenzoic acid (60%, 171 mg, 0.59 mmol. The reaction mixture was stirred at ambient temperature under nitrogen over night. The solvent was evaporated, and the residue was partitioned between 1 M sodium hydroxide and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The formed intermediate was reduced to the title compound as described for Intermediate example I-97 yielding 58 mg (46%); 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (d, 1 H), 8.58 (dd, 1 H), 8.18 (d, 1 H), 4.04-4.15 (m, 1 H), 1.79-1.93 (m, 4 H), 1.52-1.72 (m, 4 H); MS (APPI/APCI) m/z 256[M+H+].

Workup

  1. stirringthe reaction mixture was stirred at ambient temp over night
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography
  5. customyielded a colourless oil
  6. stirringThe reaction mixture was stirred at ambient temperature under nitrogen over night
  7. customThe solvent was evaporated
  8. customthe residue was partitioned between 1 M sodium hydroxide and ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fa1260618f3429cb3ef5c28b7082912
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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