Pyridine → HCID 86734638, compound

HRID 328352Notes

Reaction equation

HRID 328352 reaction equation
[OH:1][C@:2]12[C@@H:15]3[NH:16][CH2:17][CH2:18][C@:7]1([C:8]1[CH:9]=[C:10]([O:19][CH3:20])[CH:11]=[CH:12][C:13]=1[CH2:14]3)[CH2:6][CH2:5][CH2:4][CH2:3]2.N1C=CC=CC=1.[CH:27]1([C:31](O)=[O:32])[CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[CH:27]1([C:31]([N:16]2[CH2:17][CH2:18][C@@:7]34[C:8]5[CH:9]=[C:10]([O:19][CH3:20])[CH:11]=[CH:12][C:13]=5[CH2:14][C@@H:15]2[C@:2]3([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6]4)=[O:32])[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 19494Cyclobutanecarboxylic acidHCID 10901772HCID 10901772, compound

Product 1

HCID 86734638HCID 86734638, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled solution of 400 mg. (0.00146 mole) of the amino alcohol XXI in 0.16 g. (0.002 mole) of dry pyridine and 5 ml. of methylene chloride, there was added, dropwise, a solution of 0.19 g. (0.0016 mole) of the acid chloride of cyclobutylcarboxylic acid in 5 ml. of methylene chloride. After stirring for ten minutes, the reaction mixture was washed successively with cold dilute aqueous hydrochlorid acid, dilute aqueous sodium hydroxide, water and finally with a saturated aqueous sodium chloride solution. After drying over Na2SO4 and evaporation of the solvent, there was obtained 400 mg. of an oil which crystallized on standing. The oil was treated with a small amount of cold ether and filtered to yield 320 mg. (61.6 %) of crystals which after recrystallization from methanol melted at 183°-85° C. The IR and NMR spectra were consistent with the structure.

Workup

  1. temperaturecooled solution of 400 mg
  2. stirringAfter stirring for ten minutes
  3. washthe reaction mixture was washed successively with cold dilute aqueous hydrochlorid acid, dilute aqueous sodium hydroxide, water and finally with a saturated aqueous sodium chloride solution
  4. dry with materialAfter drying over Na2SO4 and evaporation of the solvent
  5. customthere was obtained 400 mg
  6. customof an oil which crystallized
  7. additionThe oil was treated with a small amount of cold ether
  8. filtrationfiltered
  9. customto yield 320 mg
  10. custom(61.6 %) of crystals which after recrystallization from methanol melted at 183°-85° C

Sources & evidence

ORD record
ord-7e69d1408c90419f8d774ebd906a8a2b
Source dataset
uspto-grants-1977_04
Patent number
US04017497

Reaction notes

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