Acetonitrile → HCID 59201237, compound

HRID 1942299Notes

Reaction equation

HRID 1942299 reaction equation
FS([C:5]([F:10])([F:9])C(O)=O)(=O)=O.[OH:11][CH2:12][C@H:13]([N:19]1[CH2:24][CH2:23][C@@H:22]([CH2:25][C:26]([OH:28])=[O:27])[CH2:21][C@H:20]1[C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=1)[CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:46]C#N>>[F:9][CH:5]([F:10])[O:11][CH2:12][C@H:13]([N:19]1[CH2:24][CH2:23][C@@H:22]([CH2:25][C:26]([O:28][CH3:46])=[O:27])[CH2:21][C@H:20]1[C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][CH:30]=1)[CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 24436Sodium SulfateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 59201214HCID 59201214, compound

Product 1

HCID 59201237HCID 59201237, compound

Conditions

Temperature
50 °C

Procedure

2-(Fluorosulphonyl)difluoroacetic acid (0.040 ml, 0.385 mmol) was added to a stirred solution/suspension of methyl {(2S,4R)-1-[(1R)-1-(hydroxymethyl)-4-methylpentyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate (Example 29, Step 1, 160 mg, 0.385 mmol) and Na2SO4 (11 mg, 0.077 mmol) in dry CH3CN (1 ml) at RT under N2. The reaction was then stirred and heated at 50° C. After 2 hours, the reaction was allowed to cool to RT, then partitioned between DCM/H2O. The aqueous layer was extracted with DCM (×2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 4-6-10% EtOAc/isohexanes) to give the title compound (13 mg) as an oil. M/Z 466 (MH+).

Workup

  1. temperatureto cool to RT
  2. custompartitioned between DCM/H2O
  3. extractionThe aqueous layer was extracted with DCM (×2)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (silica, 4-6-10% EtOAc/isohexanes)

Sources & evidence

ORD record
ord-b5f6cb879d024cbe858485d5af4a6880
Source dataset
uspto-grants-2013_03
Patent number
US08389547B2

Reaction notes

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