Hydrochloric Acid → HCID 10002276, compound

HRID 257639Notes

Reaction equation

HRID 257639 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:30]([O:32]C)=[O:31])[C:26]([O:28]C)=[O:27])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>O.CO>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:26]([OH:28])=[O:27])[C:30]([OH:32])=[O:31])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10049384HCID 10049384, compound

Product 1

HCID 10002276HCID 10002276, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of dimethyl 2-[7-(4,5-diphenyl-2-oxazolyl)heptyl]propanedioate (6.00 g, 13 mmol), 5N sodium hydroxide solution (13.4 mL), water (120 mL) and methanol (20 mL) was stirred at room temperature. After 10 minutes, the mixture was heated to reflux for 1 hour before adding water (80 mL,) and 5N NAOH solution (13 mL). After a further 3 hours at reflux, the mixture was cooled, acidified with 2N HCl solution and extracted with diethyl ether. The combined extracts were dried over sodium sulphate and the solvent evaporated to leave a white solid, 2-[7-(4,5-diphenyl-2-oxazolyl)heptyl]propanedioic acid (5.65 g, 100%). An analytical sample was prepared by recrystallizing 1.15 g from a mixture of CH2Cl2, diethyl ether and hexane to give pure product (1.05 g), m.p. 115°-117° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter a further 3 hours at reflux
  4. temperaturethe mixture was cooled
  5. extractionextracted with diethyl ether
  6. dry with materialThe combined extracts were dried over sodium sulphate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-45d232ce17b242e6a59d058867b6c52d
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

Loading…