Sodium Cyanide → HCID 21224101, compound

HRID 1584414Notes

Reaction equation

HRID 1584414 reaction equation
C[O:2][C:3]([C:5]1([CH2:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:10][CH2:9][O:8][CH2:7][CH:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[I-].[Li+].[C-]#N.[Na+]>CN(C)C=O>[CH2:11]([CH:6]1[C:5]([CH2:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)=[CH:24][CH:23]=2)(=[O:21])=[O:20])([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][O:8][CH2:7]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 66321Lithium iodideHCID 70049710HCID 70049710, compound

Product 1

HCID 21224101HCID 21224101, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-benzyl-4-[4-(4-chlorophenoxy)-phenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl ester (410 mg, 0.80 mmol) in N,N-dimethylformamide (4 mL) was added lithium iodide (1.06 g, 7.96 mmol), followed by sodium cyanide (78 mg, 1.59 mmol). The mixture was heated to 120° C. for 8 hours, cooled to room temperature, the N,N-dimethylformamide solvent removed by heating under reduced pressure, and the residue partitioned between ethyl acetate (150 mL) and saturated aqueous sodium bisulfite (50 mL). The ethyl acetate layer was dried over magnesium sulfate, concentrated in vacuo, purified by preparative chromatography (20×40-1000 um plates), eluted with 8% methanol/methylene chloride) to afford 317 mg (80%) of 3-benzyl-4-[4-(4-chlorophenoxy)-phenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid 1HNMR (N,N-dimethylformamide contaminant, CDCl3) δ 1.74 (dm, J=13.5 Hz, 1H), 2.05-2.18 (m, 2H), 2.42 (dm, J=13.5 Hz, 1H), 3.22-3.26 (m, 2H), 3.48-3.58 (m, 2H), 3.78-4.18 (m, 5H), 6.83-6.88 (m, 4H), 6.93 (d, J=8.5 Hz, 2H), 7.08-7.13 (m, 3H), 7.36 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H); CIMS (NH3, M+ +NH4 +): 518.

Workup

  1. temperaturecooled to room temperature
  2. customthe N,N-dimethylformamide solvent removed
  3. temperatureby heating under reduced pressure
  4. customthe residue partitioned between ethyl acetate (150 mL) and saturated aqueous sodium bisulfite (50 mL)
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by preparative chromatography (20×40-1000 um plates)
  8. washeluted with 8% methanol/methylene chloride)

Sources & evidence

ORD record
ord-47cbde22906844edb8625da4c4b63795
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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