Dipropylamine → HCID 67163809, compound

HRID 68643Notes

Reaction equation

HRID 68643 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)(=O)=O.[CH2:22]([NH:25][CH2:26][CH2:27][CH3:28])[CH2:23][CH3:24].O.C(=O)(O)[O-].[Na+]>C(O)(C)C>[CH2:22]([N:25]([CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 86225473Methyl 4-({5-[(methylsulfonyl)oxy]pentyl}oxy)benzoateHCID 86585896Sodium bicarbonate water

Product 1

HCID 67163809HCID 67163809, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of the compound 25 (3.70 g) and dipropylamine (3.00 mL) in isopropyl alcohol (40 mL) was stirred at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and saturated sodium bicarbonate water (40 mL) was added. The aqueous layer was extracted twice with ethyl acetate (50 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol=10:90→0:100) to obtain the title compound (1.94 g) having the following physical properties.

Workup

  1. extractionThe aqueous layer was extracted twice with ethyl acetate (50 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=10:90→0:100)

Sources & evidence

ORD record
ord-269b692578c940478895e4b2470b1403
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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