Sodium Carbonate → 2-(3-Phenyl-4,5-dihydro-1,2-oxazol-5-yl)acetic acid

HRID 1873801Notes

Reaction equation

HRID 1873801 reaction equation
Cl[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.[C:9]([O-:14])(=[O:13])[CH2:10][CH:11]=[CH2:12].C(=O)([O-])[O-].[Na+].[Na+].[CH2:21]1[CH2:25]OC[CH2:22]1.[OH2:26]>CN(C=O)C>[CH2:12]1[C:6]([C:5]2[CH:25]=[CH:21][CH:22]=[CH:3][CH:4]=2)=[N:2][O:26][CH:11]1[CH2:10][C:9]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31398ChlorosuccinimideHCID 69710893-Butenoic acid, ion(1-)HCID 21881883Oxolane--water (1/1)

Product 1

HCID 107982712-(3-Phenyl-4,5-dihydro-1,2-oxazol-5-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzaldehyde (1, 32.8 mmol) and hydroxylamine hydrochloride (33 mmol) were dissolved in methanol (100 ml) followed by addition of sodium carbonate (65 mmol). Overnight reaction gave the oxime derivative in 95% (2, 30.4 mmol). Chlorination of the oxime using N-chlorosuccinimide (31.6 mmol) in DMF (100 ml) quantitatively furnished chlorooxime (3). Compound 3 was then dissolved in THF/H2O (*0/20) and treated with 3-butenoate (24.5 mmol) and sodium carbonate (73.6 mmol). After completion, (12 h), the product was extracted with ethyl acetate and the organic extracts were washed with brine and dried over magnesium sulfate. GIT-27 was crystallized from ethyl acetate/heptane mixture. The structure was confirmed by 1H-NMR, 13C-NMR and mass spectroscopy. The daily dosage regimen will presumably vary within wide ranges, for instance from 0.1 to 10 mg/kg body weight.

Workup

  1. extractionAfter completion, (12 h), the product was extracted with ethyl acetate
  2. washthe organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customGIT-27 was crystallized from ethyl acetate/heptane mixture

Sources & evidence

ORD record
ord-e6fd3210cde2411094115aa794a82c5c
Source dataset
uspto-grants-2012_11
Patent number
US08304442B2

Reaction notes

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