Hydrochloric Acid → HCID 59027827, compound

HRID 1037671Notes

Reaction equation

HRID 1037671 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[O:11][CH:12]=2)=[CH:4]1.Cl>O.CO>[S:3]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[O:11][CH:12]=2)=[CH:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59027823HCID 59027823, compound

Product 1

HCID 59027827HCID 59027827, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Add solution of sodium hydroxide in water to a solution of methyl 5-(4-thiophen-3-yloxazol-2-yl)pentanoate in methanol at room temperature and heat the mixture at 40° C. for 2 hours. Adjust the pH of the mixture to 2 with 1 N HCl and extract with ethyl acetate. Wash the organic extract three times with water, dry over sodium sulfate and remove the solvent under reduced pressure. Triturate the residue with hexanes/ethyl acetate and collect the solids by filtration to provide the title compound: APCI mass spectrum m/z 252 [C12H13NO3S+H]+.

Workup

  1. extractionextract with ethyl acetate
  2. washWash the
  3. extractionorganic extract three times with water
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customTriturate the residue with hexanes/ethyl acetate
  7. customcollect the solids
  8. filtrationby filtration

Sources & evidence

ORD record
ord-19110a1bbbcb46e992d9f145d1ace2e9
Source dataset
uspto-grants-2013_10
Patent number
US08546581B2

Reaction notes

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