Isopropylamine → HCID 9838564, compound

HRID 647909Notes

Reaction equation

HRID 647909 reaction equation
[CH:1]([C:3]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[CH:31]([NH2:34])([CH3:33])[CH3:32]>ClCCl.CCOCC.Cl>[CH:31]([NH:34][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:3]=1[CH:1]=[O:2])([CH3:33])[CH3:32]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 721625-(2-Formyl-3-hydroxyphenoxy)pentanoic acid

Product 1

HCID 9838564HCID 9838564, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5-(2-Formyl-3-hydroxyphenoxy)pentanoic acid (595 mg, 2.5 mM) was dissolved in dry dichloromethane (7.5 ml) under nitrogen with stirring, and immersed in a cooling bath kept at -10° C. To this solution was added dropwise from a syringe triethylamine (0.35 ml, 2.5 mM). After 5 minutes was then similarly added ethyl chloroformate (0.25 ml, 2.5 mM). After 15 minutes was then similarly added isopropylamine (0.215 ml, 2.5 mM). The reaction mixture was allowed to warm to room temperature and then stirred at room temperature (1/2 hr). After diluting with ether (50 ml) and 1 N hydrochloric acid the aqueous phase was removed and the organic phase washed with dilute sodium bicarbonate solution and then quickly extracted with 2 N sodium hydroxide solution (1×25 ml). The layers were separated and the aqueous phase immediately acidified with dilute hydrochloric acid and extracted with ether/ethyl acetate. The combined extracts were washed with dilute sodium bicarbonate solution, water, dried (sodium sulphate) and evaporated to give N-isopropyl 5-(2-formyl-3-hydroxyphenoxy)pentanamide, m.p. 92°-93° C. from ethyl acetate/petrol.

Workup

  1. customimmersed in a cooling bath
  2. customkept at -10° C
  3. waitAfter 15 minutes was
  4. stirringstirred at room temperature (1/2 hr)
  5. customwas removed
  6. washthe organic phase washed with dilute sodium bicarbonate solution
  7. extractionquickly extracted with 2 N sodium hydroxide solution (1×25 ml)
  8. customThe layers were separated
  9. extractionextracted with ether/ethyl acetate
  10. washThe combined extracts were washed with dilute sodium bicarbonate solution, water
  11. dry with materialdried (sodium sulphate)
  12. customevaporated

Sources & evidence

ORD record
ord-691451ce654e4ca5a7f8f01c1f9645e9
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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