Methyl iodide → HCID 67342524, compound

HRID 1669275Notes

Reaction equation

HRID 1669275 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH2:7][CH2:8][NH:9][C:10](=[O:42])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:46]I>CN(C)C=O>[C:1]([O:5][C:6](=[O:43])[CH2:7][CH2:8][N:9]([C:10](=[O:42])[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)=[CH:30][CH:31]=2)[CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:15][CH:16]=1)[CH3:46])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59729396HCID 59729396, compound

Product 1

HCID 67342524HCID 67342524, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid tert-butyl ester (0.0910 g, 0.153 mmol) in dimethylformamide (1.0 mL) at 0° C. was treated with NaH (1 small spatula tip). After 25 min., MeI (0.0240 mL, 0.385 mmol) is added and the reaction is stirred for 1 h. The reaction mixture is quenched with saturated NH4Cl (aq) (2 μL) and extracted with EtOAc (3×10 mL). Combined extracts are washed with brine (1×), dried over MgSO4, filtered, and conc. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 10% EtOAc to 60% EtOAc giving (±)-3-({4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoyl}-methyl-amino)-propionic acid tert-butyl ester (7.4 mg, 8%) as a clear syrup. MS (ES): 554.0 [M+H-(t-Bu)]+.

Workup

  1. customThe reaction mixture is quenched with saturated NH4Cl (aq) (2 μL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washCombined extracts are washed with brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. washeluted with hexanes using a gradient of 10% EtOAc to 60% EtOAc

Sources & evidence

ORD record
ord-a7a2058b695c4396b55c9102e61b84b8
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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