Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid

HRID 1189361Notes

Reaction equation

HRID 1189361 reaction equation
N#N.C[O:4][C:5]([C:7]1[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2([CH3:21])[O:20][CH2:19][CH2:18][O:17]2)[O:10][CH:11]=1)=[O:6].[OH-].[Na+]>C1COCC1>[CH3:21][C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][C:9]2[O:10][CH:11]=[C:7]([C:5]([OH:6])=[O:4])[N:8]=2)[O:20][CH2:19][CH2:18][O:17]1

Participants

5

Reactant 3

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 671288542-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid methyl ester

Product 1

HCID 671284612-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid methyl ester (713 mg, 2.65 mmol) in THF (15 mL) was treated at rt with 1N NaOH (6.7 mL, 6.70 mmol) and the reaction mixture was stirred for 1 h at rt. The solvents were removed under reduced pressure. The residue was treated with sat. aq. NH4Cl, and acidified to pH 4-5 with 1N HCl. The aq. layer was extracted with CH2Cl2 and the combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a white solid. TLC: rf (4:1 CH2Cl2-MeOH)=0.5. LC-MS-conditions 02: tR=0.75 min [M+H]+=256.31.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionThe residue was treated with sat. aq. NH4Cl
  3. extractionThe aq. layer was extracted with CH2Cl2
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-74af245ba594494683e69bc56d6fa054
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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