Water → HCID 18663507, compound

HRID 1957034Notes

Reaction equation

HRID 1957034 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:28][N:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)[CH3:2].[CH3:30]I.[H-].[Na+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[O:28][N:27]=[CH:26][CH:25]=2)=[CH:22][CH:23]=1)[N:6]([C:7](=[O:16])[C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1)[CH3:30])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53708079HCID 53708079, compound

Product 1

HCID 18663507HCID 18663507, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3,5-dimethylbenzoyl)-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester (3,8 g) and methyliodide (1.8 ml) in dry N,N-dimethylformamide (40 ml) is cooled in an ice bath and sodium hydride (60% in oil, 390 mg) is added in portions. The mixture is allowed to warm to room temperature during 5 hours, then poured into water, extracted with ethyl acetate, the organic phase washed with water, and with brine, dried and evaporated. Flash chromatography of the residue on silica gel (hexane/ethyl acetate 3:1) gives pure N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester. NMR (CDCl3, 400 MHz) δ [ppm] 8.30 (d, broad, 1H), 7.75 (m, 2H), 7.41 (d, broad, 1H), 7.12 (d, broad, 1H), 6.97 (s, 0.5H), 6.93 (s, 0.5 H), 6.70 (s, 1H), 6.53 (d, broad, 1H), 6.36 (d, broad, 1H), 5.40 (m, 0.5H), 4.58 (m, 0.5H), 4.27 (m, 2H), 3.54 (m, 0.5H), 3.25 (m, 1H), 3.05 (m, 2H), 2.78 (s, 1.5H), 2.23 (s, 3H), 2.13 (s, 3H), 1.27 (m, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase washed with water
  3. dry with materialwith brine, dried
  4. customevaporated

Sources & evidence

ORD record
ord-ee6a55a904254a7898327a84c2093bf1
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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