Diisopropylethylamine → HCID 22315130, compound

HRID 398502Notes

Reaction equation

HRID 398502 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH:28]1([CH2:33][CH:34]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=2)[C:35]([OH:37])=O)[CH2:32][CH2:31][CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C.[NH2:55][C:56]1[O:57][CH:58]=[CH:59][N:60]=1>CN(C)C=O>[CH:28]1([CH2:33][CH:34]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=2)[C:35]([NH:55][C:56]2[O:57][CH:58]=[CH:59][N:60]=2)=[O:37])[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5585212-AminooxazoleHCID 27627253-cyclopentyl-2-(3,4-dichlorophenyl)propanoic Acid

Product 1

HCID 22315130HCID 22315130, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (102 mg, 0.23 mmol), 3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid (prepared as in Example 38A, 60 mg, 0.21 mmol), N,N-diisopropylethylamine (73 μL, 0.42 mmol), and 2-aminooxazole (27 mg, 0.31 mmol) in dry N,N-dimethylformamide (1 mL) was stirred at 25° C. under nitrogen for 15 h. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed sequentially with a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-oxazol-2-yl-propionamide (34.9 mg, 47%) as a white solid: mp 134-136° C.; EI-HRMS m/e calcd for C17H18Cl2N2O2 (M+) 352.0745, found 352.0750.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed sequentially with a 1N aqueous hydrochloric acid solution, water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5133ad4cd19948dd9c9e3d30fccc94ad
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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