Triethylamine → HCID 21294064, compound

HRID 543230Notes

Reaction equation

HRID 543230 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](O)=[O:14])=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2].Cl.[NH2:23][OH:24].C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:23][OH:24])=[O:14])=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 13753872HCID 13753872, compound

Product 1

HCID 21294064HCID 21294064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Four and six-tenths grams of 5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentanoic acid were converted to the corresponding acid chloride according to the procedure of Example 55. The resulting acid chloride and 1.05 g. of hydroxylamine hydrochloride were dissolved in 50 ml. of methylene chloride, after which were added 4.15 ml. of triethylamine in about 50 ml. of methylene chloride. After stirring overnight at room temperature, the methylene chloride was removed by evaporation and the residue was partitioned between acetate and dilute hydrochloric acid. The layers were separated, and the ethyl acetate solution was evaporated in vacuo. The residue was dissolved in diethyl ether and the solution was extracted with dilute sodium hydroxide solution. The aqueous basic solution was then made acidic with dilute hydrochloric acid and the solution was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and evaporated to dryness. The residue was crystallized from methylene chloride/hexane to provide 400 mg. of the title product.

Workup

  1. customthe methylene chloride was removed by evaporation
  2. customthe residue was partitioned between acetate and dilute hydrochloric acid
  3. customThe layers were separated
  4. customthe ethyl acetate solution was evaporated in vacuo
  5. dissolutionThe residue was dissolved in diethyl ether
  6. extractionthe solution was extracted with dilute sodium hydroxide solution
  7. extractionmade acidic with dilute hydrochloric acid and the solution was extracted with ethyl acetate
  8. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  9. customevaporated to dryness
  10. customThe residue was crystallized from methylene chloride/hexane
  11. customto provide 400 mg

Sources & evidence

ORD record
ord-a5be5012144042caae267d19e67ff6f7
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

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