Potassium Carbonate → 4-Carboxy-N-(2,2-dimethyl-3-nitroxypropionyl)-2-phenylthiazolidine

HRID 1770213Notes

Reaction equation

HRID 1770213 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:6][O:7][N+:8]([O-:10])=[O:9])[C:3](Cl)=[O:4].[C:12]([CH:15]1[CH2:19][S:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:16]1)([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[C:12]([CH:15]1[CH2:19][S:18][CH:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:16]1[C:3](=[O:4])[C:2]([CH3:11])([CH3:1])[CH2:6][O:7][N+:8]([O-:10])=[O:9])([OH:14])=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 392372-Phenylthiazolidine-4-carboxylic acidHCID 200955153-Chloro-2,2-dimethyl-3-oxopropyl nitrate

Product 1

HCID 677785314-Carboxy-N-(2,2-dimethyl-3-nitroxypropionyl)-2-phenylthiazolidineYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.2 g of 2,2-dimethyl-3-nitroxypropanoyl chloride in 100 ml of tetrahydrofuran was added at 0° C. under nitrogen to a solution of 6.0 g of 4-carboxy-2-phenylthiazolidine and 4.0 g of potassium carbonate in a mixture of 50 ml of tetrahydrofuran and 150 ml of water. After stirring the resulting solution for 45 minutes the mixture was concentrated under reduced pressure to about 150 ml and then acidified to pH=2 with citric acid. The resulting mixture was extracted with diethyl ether and the organic phase was dried over sodium sulphate and evaporated. The residue was purified by chromatography (silica, petroleum ether 60-80: ethyl acetate: acetic acid/8:8:1). Yield 38%. Empirical formula C15H18N2O6S. Molecular weight 354. Melting point 35°-38° C. TLC system: petroleum ether 60-80: ethyl acetate: acetic acid/4:4:1. Rf 0.50.

Workup

  1. concentrationwas concentrated under reduced pressure to about 150 ml
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, petroleum ether 60-80: ethyl acetate: acetic acid/8:8:1)

Sources & evidence

ORD record
ord-707e8f9929274e4d80a83760980aa464
Source dataset
uspto-grants-1995_01
Patent number
US05385922

Reaction notes

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