Hydrochloric Acid → HCID 86744541, compound

HRID 704607Notes

Reaction equation

HRID 704607 reaction equation
[CH2:1]([N:5]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[C:12](\[CH2:18][P:19]([O:25]CC)([CH2:21][CH:22]([CH3:24])[CH3:23])=[O:20])/[C:13]([O:15]CC)=[O:14])[CH2:2][CH2:3][CH3:4].CO.O.[ClH:35]>>[ClH:35].[CH2:28]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[C:12](\[CH2:18][P:19]([OH:25])([CH2:21][CH:22]([CH3:24])[CH3:23])=[O:20])/[C:13]([OH:15])=[O:14])[CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 15735637HCID 15735637, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 86744541HCID 86744541, compoundYield 94%

Conditions

Temperature
90 °C

Procedure

Ethyl (Z)-8-dibutylamino-2-(ethoxyisobutylphosphinoyl)methyl-2-octenoate (200 mg; 0.43 millimole) was dissolved in 5 ml of concentrated hydrochloric acid, and the solution was stirred at 90° C. for 5.5 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was purified by medium-pressure liquid chromatography [Lobar column (a product of E. Merck & Co.), size B, Lichroprep RP-18, methanol/water (7:3)] to give 178 mg (yield 94%) of the captioned compound as a pale yellow oil.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by medium-pressure liquid chromatography [Lobar column (a product of E

Sources & evidence

ORD record
ord-7dbe27660f4040179309e530ad429a9e
Source dataset
uspto-grants-1991_01
Patent number
US04988681

Reaction notes

Loading…