Hydrochloric Acid → HCID 54463598, compound

HRID 1086595Notes

Reaction equation

HRID 1086595 reaction equation
C(N(CC)CC)C.[NH2:8][CH:9]([C:18]([O:20]CC)=[O:19])[CH2:10][CH:11]=[CH:12][CH2:13][C:14]([O:16]C)=[O:15].C([O:25][C:26](=[O:32])[CH2:27][CH2:28][C:29](Cl)=[O:30])C.Cl>C(Cl)Cl.O>[OH:32][C:26](=[O:25])[CH2:27][CH2:28][C:29]([NH:8][CH:9]([C:18]([OH:20])=[O:19])[CH2:10][CH:11]=[CH:12][CH2:13][C:14]([OH:16])=[O:15])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 53667645HCID 53667645, compound

Product 1

HCID 54463598HCID 54463598, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

338 mg of triethylamine were added at ambient temperature to 583 mg of 1-methyl 7-ethyl 6-amino-3-heptenedioate prepared as in Example 5D in 50 ml of methylene chloride and after the mixture was cooled to +5° C., 483 mg of ethyl4-chloro-4-oxo-butanoate were added. The mixture was stirred for 1 hour at ambient temperature and 25 ml of water and 1 ml of 2N hydrochloric acid were added. Extraction was done with methylene chloride and the extract was washed with salt water, then with sodium bicarbonate solution, dried and the solvents were evaporated. The residue was chromatographed on silica and elution with cyclohexane - ethylene acetate (1-1) yielded 750 mg of the expected product.

Workup

  1. temperatureafter the mixture was cooled to +5° C.
  2. extractionExtraction
  3. washthe extract was washed with salt water
  4. dry with materialwith sodium bicarbonate solution, dried
  5. customthe solvents were evaporated
  6. customThe residue was chromatographed on silica and elution with cyclohexane - ethylene acetate (1-1)

Sources & evidence

ORD record
ord-dabbcec50b0d4d9e939789f5b38bc1a4
Source dataset
uspto-grants-1991_07
Patent number
US05030715

Reaction notes

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