Propionic Acid → HCID 11716950, compound

HRID 898185Notes

Reaction equation

HRID 898185 reaction equation
C1[N:5]=[C:4]([NH2:6])[S:3]C=1.[CH2:7](N(CC)CC)[CH3:8].CN([P+](O[N:25]1[N:33]=[N:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[C:41]([OH:45])(=O)[CH2:42][CH3:43].[C:46]([O:49][CH2:50][CH3:51])(=O)C>CN(C=O)C>[N:32]([CH2:27][CH2:28][C:29]1[S:3][C:4]([NH:6][C:41](=[O:45])[CH2:42][CH3:43])=[N:5][C:30]=1[C:31]1[CH:26]=[CH:51][C:50]([O:49][CH3:46])=[CH:8][CH:7]=1)=[N+:33]=[N-:25]

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 21552-AminothiazoleHCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 11716950HCID 11716950, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the aminothiazole 3A (203 mg, 0.57 mmol) and triethylamine (0.238 mL, 1.71 mmol) in dry DMF (6 mL) was treated with BOP reagent (504 mg, 1.41 mmol) and propionic acid (0.127 mL, 1.71 mmol). The mixture was stirred at room temperature for 15 h, then partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was washed with water (20 mL), 1 N aqueous HCl (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (10 mL), then dried over sodium sulfate and concentrated. Flash column chromatography (silica, 30% ethyl acetate in hexanes to 35% ethyl acetate in hexanes) provided the title compound as an oil (132 mg, 70% yield). MS m/e 332; HPLC retention time 3.38 min.

Workup

  1. custompartitioned between ethyl acetate (20 mL) and water (20 mL)
  2. washThe organic layer was washed with water (20 mL), 1 N aqueous HCl (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a0a2a24dd9541408a267626d4b8a356
Source dataset
uspto-grants-2008_04
Patent number
US07351727B2

Reaction notes

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