Potassium Carbonate → HCID 68283204, compound

HRID 623993Notes

Reaction equation

HRID 623993 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[N+:21]([CH2:23][C:24]([O:26][CH3:27])=[O:25])#[C-:22].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.C1(C)C=CC=CC=1.CCOC(C)=O>[N:1]1([C:6]2[CH:7]=[C:8]([C:9]3[O:11][CH:22]=[N:21][C:23]=3[C:24]([O:26][CH3:27])=[O:25])[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 547815Methyl isocyanoacetateHCID 6517213-pyrrolidin-1-ylbenzoic acid

Product 1

HCID 68283204HCID 68283204, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 21584019Toluene ethylacetateSolvent

Procedure

To a suspension of 3-(pyrrolidin-1-yl)benzoic acid (1.0 g, 5.23 mmol) and K2CO3 1.75 g (12.55 mmol) in DMF (10.8 ml) was added methyl isocyanoacetate (551 mg, 5.23 mmol) in DMF (6.8 mL). The resulting mixture was stirred at rt for 5 min and then cooled to 0° C. A solution of DPPA (1.13 mL, 5.23 mmol) in DMF (6.8 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 2 h and then at rt overnight. It was then diluted with toluene-EtOAc 1:1 (110 mL) and the organic layer was washed with water (55 mL) and aq. sat. NaHCO3-solution (45 mL), dried (MgSO4), filtered and concentrated to dryness. The residue was purified by FC (DCM/MeOH 9:1; Rf=0.41) to afford methyl 5-(3-(pyrrolidin-1-yl)phenyl)oxazole-4-carboxylate as a orange oil. LC-MS conditions A: tR=0.93 min, [M+H]+=273.04.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe resulting mixture was stirred at 0° C. for 2 h
  3. customat rt
  4. customovernight
  5. washthe organic layer was washed with water (55 mL) and aq. sat. NaHCO3-solution (45 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by FC (DCM/MeOH 9:1; Rf=0.41)

Sources & evidence

ORD record
ord-d306a390cc41499e8af80cf79b01dc01
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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