2-(3-Methyl-1,2-oxazol-5-yl)acetic acid → HCID 68352056, compound

HRID 2174554Notes

Reaction equation

HRID 2174554 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:23]([O:25][CH3:26])=[O:24].[CH3:27][C:28]1[CH:32]=[C:31]([CH2:33][C:34](O)=[O:35])[O:30][N:29]=1>O=P(Cl)(Cl)Cl>[Cl:8][C:6]1[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]([C:23]([O:25][CH3:26])=[O:24])=[C:2]([NH:1][C:34](=[O:35])[CH2:33][C:31]2[O:30][N:29]=[C:28]([CH3:27])[CH:32]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acidHCID 68352050HCID 68352050, compound2×

Product 1

HCID 68352056HCID 68352056, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of methyl 4-amino-6-chloro-4″-methoxy-[1,1′:4′,1″-terphenyl]-3-carboxylate (Intermediate 49) (520 mg, 1.41 mmol)) and 2-(3-methylisoxazol-5-yl) acetic acid (Aldrich, 219 mg, 1.56 mmol) in POCl3 (6 mL) was heated at 80° C. for 2 h and then cooled to room temperature. The solution was concentrated under reduced pressure. The crude material was taken up with ethyl acetate and saturated NaHCO3, the organic phase was washed with water and dried over Na2SO4 and the solvent removed under reduced pressure. The crude material was purified on silica gel column chromatography using cyclohexane to cyclohexane/ethyl acetate 75:25 as eluant to give the title compound methyl 6-chloro-4″-methoxy-4-(2-(3-methylisoxazol-5-yl)acetamido)-[1,1′:4′,1″-terphenyl]-3-carboxylate (210 mg, 0.43 mmol, 30.4%). LCMS: (M+H)+=491; Rt=1.37 min.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe solution was concentrated under reduced pressure
  3. washthe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. customThe crude material was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-d55889f7fe3a41be984cd9ab7dd7d6d6
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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